Mixtures of imidazoline quaternary ammonium and alkyl quaternary ammonium compounds

ABSTRACT

Compositions that include mixtures of (a) at least one dialkyl quat in the amount of from about 10% to about 90% by weight of the composition; and (b) at least one monoalkyl quat in the amount of from about 10% to about 90% by weight of the composition are provided. Various embodiments are provided. In one embodiment, the mixtures include dialkyl immidazoline quats and monoalkyl immidazoline quats. In one embodiment, the mixtures include dialkyl immidazoline quats and monoalkyl ammonium quats. Various methods of making immidazoline quats and quat mixtures, personal care and cosmetic products and formulations that contain the immidazoline quats and quat mixtures, methods of making such personal care and cosmetic products and formulations, and methods of using the such immidazoline quats, quat mixtures, and personal care and cosmetic products and formulations are also provided.

CROSS REFERENCE TO CROSS-REFERENCE TO RELATED APPLICATIONS

This patent application claims the benefit of the filing date of theU.S. Provisional Application No. 60/347,005, filed Jan. 9, 2002, and thebenefit of the filing date of the U.S. Provisional Application No.60/403,041, filed Aug. 13, 2002, the disclosures of both of which arehereby incorporated by reference in their entirety.

FIELD OF THE INVENTION

The present invention relates to the field of chemical manufacture andin particular, personal care products and cosmetics. It providescompositions that include quaternary compounds various personal care andcosmetic products, formulations that include such compositions, as wellas methods of their manufacture, use, and other related methods.

BACKGROUND OF THE INVENTION

Emulsions and Emulsification

An emulsion, more precisely a liquid/liquid emulsion, is a two-phasesystem of two immiscible liquids (usually, incompletely immiscible),with one of the phases being dispersed in the form of droplets in theother phase. Emulsions are preferred forms for the cosmetic and personalcare products because they allow for the combination of otherwiseimmiscible ingredients and can provide significant economic advantages.Also, the public favors the feel and look of the emulsions. For thesereasons, among others, a large proportion of modern cosmetic andpersonal care products are emulsions, and the process of producingemulsions (or emulsification) is a very important process in thecosmetic and personal care industries.

As described, emulsions' two liquid phases do not form a single phaseupon mixing. It is believed that the primary reason for thisimmiscibility is the difference in the polarity of the molecules thatcomprise each liquid phase. Usually, one phase is relatively lipophilicor non-polar, while the other is relatively hydrophilic or polar.

If the phases (e.g., water and oil) are combined without any agitation,they usually (although not necessarily) form two separate layers with asingle phase-separation boundary between the layers. Emulsificationtypically involves agitation to disperse one phase throughout the other.Such dispersion leads to an increase in the area of surface contactbetween the phases, which have drastically different polarities. It isbelieved that the increase in the area of surface contact increasessurface tension or surface energy of the phases.

For this reason, most emulsions are thought to be thermodynamicallyunfavorable and therefore inherently unstable after formation. Tominimize the area of surface contact and the surface energy when leftalone over time, emulsions tend to separate back into two layers with asingle phase-separation boundary.

Since the products formulated as emulsions are usually stored forsubstantial periods of time prior to use, this separation of phases ishighly undesirable. To prevent phase separation, formulators usually addvarious emulsifiers. The emulsifiers are surface-active compounds orsurfactants that are believed to reduce the surface tension of thephases, thus reducing the thermodynamic drive for phase separation andimproving the stability of emulsions.

The emulsifiers are usually compounds having both hydrophilic andlipophilic groups in the molecule. Somewhat oversimplifying, thehydrophilic groups contact the hydrophilic phase of the emulsion, andthe lipophilic groups contact the lipophilic phase, in effect tying thephases together and acting to prevent phase separation. The selectionand utilization of emulsifiers is one of the challenges in formulatingemulsions.

Quaternary compounds

Personal care and cosmetic products often contain various surfactants,including cationic surfactants having a quaternary nitrogen atom (orquats). Quats are commonly used in hair care products. It is known thathair may be negatively affected by atmospheric agents, chemicaltreatments, and the like, resulting in damaged hair, which lackssoftness and which may be difficult to disentangle or style. Quatsfacilitate disentangling and combing of hair, and provide softness tothe hair, and thus they are used as active ingredients of hair careproducts, such as hair conditioners and conditioning shampoos.

Various types of quats are known in the art. Ammonium quats that containquaternized ammonium nitrogen

are described, for example, in U.S. Pat. Nos. 4,954,335 and 4,891,214.Examples of such quats include diphenyl dimethyl ammonium quat soldunder the trade name INCROQUAT DBM-90 from Croda Incorporated, 7 CenturyDrive, Parsippany, N.J. 07054. Other examples of ammonium quats used inhair care products are cetyltrimethylammonium bromide andbehenyltrimethylammonium bromide.

Other types of quats are also known in the art. Immidazoline-based quatscontaining the immidazoline ring

are disclosed, for example, in U.S. Pat. Nos. 4,851,141, 4,452,732,4,247,538, 4,206,195, 4,187,289, 4,149,551, and 4,102,795.

U.S. Pat. No. 4,102,795 discloses compositions for softening fabrics orhair that include immidazoline-based quarternary compounds of theformula

where R′ and R′″ are alkyl groups having 11 to 22 carbon atoms, orβ-hydroxyalkyl groups having from 13 to 24 carbon atoms; R″ is an alkylgroup having 1 to 3 carbon atoms, benzyl group, or the group—(C₂H₄O)_(n)H, where n is 1 to 3; and Y⁻ is halogen or monoalkylsulfate. The '795 patent mentions the possibility of mixtures of theseimmidazoline-based compounds, but does not provide their content orother information about such mixtures.

U.S. Pat. No. 4,452,732 discloses a shampoo containing severalcomponents, including immidazoline-based quaternary compounds of theformula

where at least one of, and preferably both of the groups Q′ and Q′″is/are a hydrocarbon group(s) containing 16 to 22 carbon atoms,preferably, 16 to 18 carbon atoms; Q″ is C₁-C₄ alkyl or hydroxyalkylgroup; and Y⁻ is a compatible anion. Mixtures are mentioned, but again,the mention is without information about their content, and no specificmixtures are disclosed.

Primarily, the immidazoline-based quats and the ammonium quats aredisclosed as pure compounds. While mixtures of quats or mixtures withdifferent surfactants had been mentioned in general, the prior artprovides no specific mixtures or other information about the mixtures.Also, the prior art does not provide information about the relationshipsbetween primary product performance, such as performance in hairconditioning products, and emulsification characteristics of quatsand/or quat mixtures in emulsion-formulated products.

SUMMARY OF THE INVENTION

The present invention relates to compositions that include certainmixtures of quats. The aspects of the invention include such mixtures ofquats, methods of making such quat mixtures, personal care and cosmeticproducts and formulations that contain these quat mixtures, methods ofmaking such personal care and cosmetic products and formulations, andmethods of using the such quat mixtures, products and formulations.

In one aspect, the invention provides compositions that include mixturesof (a) at least one dialkyl quat in the amount of from about 10% toabout 90% by weight of the composition; and (b) at least one monoalkylquat in the amount of from about 10% to about 90% by weight of thecomposition.

Various embodiments are provided. In one embodiment, the mixturesinclude dialkyl immidazoline quats and monoalkyl immidazoline quats. Inone embodiment, the mixtures include dialkyl immidazoline quats andmonoalkyl ammonium quats

Also provided is a method of improving formulation of hair conditioningproducts by providing mixtures of (a) at least one dialkyl quat in theamount of from about 10% to about 90% by weight of the composition; and(b) at least one monoalkyl quat in the amount of from about 10% to about90% by weight of the composition. The mixture of two components, whereinone component is selected for primary product performance, and anothercomponent is selected for its contribution to proper emulsification ofthe hair conditioning product but essentially does not detract from theprimary product performance. Methods of making immidazoline quats andquat mixtures, personal care and cosmetic products and formulations thatcontain the immidazoline quats and quat mixtures, methods of making suchpersonal care and cosmetic products and formulations, and methods ofusing the such immidazoline quats, quat mixtures, and personal care andcosmetic products and formulations are also provided. Variousembodiments of the methods are disclosed.

DESCRIPTION OF THE PREFERRED EMBODIMENTS

For the purposes of the present invention, various terms used herein aredefined as follows. A “compound” is a distinct chemical substance havingmolecules of the same chemical structure. A “compound” is not a mixtureof molecules having different chemical structures. A “composition” mayinclude one compound or a mixture of compounds.

An “alkyl group” is any substituent group that includes a chain of oneor more carbon atoms. An alkyl group may terminate in alkylfunctionality (e.g., —CH₃) or non-alkyl functionality (e.g., —Br).Likewise, an alkyl group may connect to the rest of the molecule (MOL)through alkyl functionality (e.g., —CH₂— in MOL-CH₂CH₃) or non-alkylfunctionality (e.g., —SO2— in MOL-SO₂C₃H₈). Purely for purposes ofillustration, each of the groups —(CH₂)₃—OH, —(CH₂)₄—CH₃, —CH₃, and—C(O)—(CH₂)₅—CH₃, is an alkyl group. An “alkyl radical” is a chain ofone or more carbon atoms connected to one another. Purely for purposesof illustration, the alkyl groups —(CH₂)₃—OH, —(CH₂)₄—CH₃, and—C(0)—(CH₂)₅—CH₃ contain alkyl radicals of the structures —(CH₂)₃—,—(CH₂)₄—CH₃, and —(CH₂)₅—CH₃, respectively.

Carbon chains of alkyl groups and alkyl radicals, and alkyl groups andradicals themselves are described as “C_(x)-C_(y).” An alkyl groupcontaining a C_(x)-C_(y) alkyl radical is referred to as C_(x)-C_(y)alkyl. Such description encompasses carbon chains of every lengthranging from x to y carbon atoms, inclusive. For example, thedescription of an alkyl radical as “C₁₀-C₂₀” encompasses all alternativecarbon chains having from 10 to 20 carbon atoms, including carbon chainshaving 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, and 20 carbon atoms.

Terms such as alkylhydroxy, alkylcarboxy, carboxyalkyl, and the like,are used throughout. Purely for purposes of illustration, analkylhydroxy group contains a hydroxy group and an alkyl radical, andconnects to the rest of the molecule through the alkyl radical; acarboxyalkyl group contains an alkyl radical and a carboxy functionalitythat connects the carboxy group to the rest of the molecule; analkylcarboxy group connects to the rest of the molecule through an alkylradical and terminates in a carboxy functionality. Purely for purposesof illustration, “C₁₀-C₃₀ alkyl” defines a range of alkyl groupscontaining alkyl radicals having from 10 to 30 carbon atoms and “C₁₀-C₃₀alkylhydroxy” defines a range of alkyl groups containing a hydroxy groupand alkyl radicals having from 10 to 30 carbon atoms.

In the compounds described herein, and consistent with the definitionsset forth above, the alkyl groups and alkyl radicals, when present, maybe substituted or unsubstituted, straight chain or branched, saturatedor unsaturated. The substituents of the alkyl groups and alkyl radicalsdescribed herein, when present, may include lower alkyl, which containalkyl radicals having from 1 to 8 carbon atoms (e.g., methyl, ethyl,n-propyl, i-propyl, and butyl); halogenated lower alkyl, such astrifluoromethyl, perfluoroethyl, chloromethyl, and dichloromethyl;arylalkyl, such as benzyl; alkylaryl, such as p-methylbenzyl; halo, suchas fluoro, chloro and bromo; carboxy, such as acetoxy and ethylcarboxy;alkylcarboxy, such as acetoxymethyl and acetoxyethyl; arylacetoxy, suchas acetylbenzyl; hydroxy; alkoxy, such as methoxy, ethoxy and propoxy;and alkylhydroxy, such as hydroxymethyl and hydroxyethyl.

Dialkyl quats are compounds the molecules of which include a quaternarynitrogen atom and two alkyl groups or alkyl radicals having 10 or morecarbon atoms. Dialkyl immidazoline quats are compounds the molecules ofwhich include an immidazoline ring, a quaternary nitrogen atom, and twoalkyl groups having 10 or more carbon atoms (two C₁₀₊ alkyl groups).Dialkyl ammonium quats are compounds the molecules of which include aquaternary ammonium nitrogen atom and two alkyl groups or alkyl radicalshaving 10 or more carbon atoms.

Monoalkyl quats are compounds the molecules of which include aquaternary nitrogen atom and one alkyl group or alkyl radical having 10or more carbon atoms. Monoalkyl immidazoline quats are compounds themolecules of which include an immidazoline ring, a quaternary nitrogenatom, and one alkyl group having 10 or more carbon atoms (one C₁₀₊ alkylgroup). Monoalkyl ammonium quats are compounds the molecules of whichinclude a quaternary ammonium nitrogen atom and one alkyl group or alkylradical having 10 or more carbon atoms.

Mixtures of quat compounds are described herein in terms of theirsubstitution content, which is a characteristic of the quat mixture as awhole. The substitution content of a quat mixture is a ratio, expressedin the percentage terms, of the molar content of the alkyl groups thatfall within a specified substitution range to the molar content of thealkyl groups that fall within a broader, reference substitution range.The molar content values for both the specified substitution range andthe reference substitution range are measured for the quat mixture as awhole.

The specified substitution ranges are denoted as “C_(x-y)”, indicating arange alkyl groups or alkyl radicals having from x to y carbon atoms.The reference substitution ranges are denoted as “C_(X-Y)” or “C₁₀₊”.“C₁₀₊” indicates a range of alkyl group or alkyl radicals having 10 ormore carbon atoms. “C_(X-Y)” indicates a range of alkyl groups or alkylradicals having from X to Y carbon atoms.

The quat mixtures are described in terms of their “C_(x-y) content” or“C_(x-y) substitution content”. The C₁₀₊ reference range is the defaultsubstitution range. Thus, unless specified otherwise, a C_(x-y)substitution content of a quat mixture (abbreviated in the exemplifiedmixtures throughout as “S_(x-y)”) is the ratio, expressed in thepercentage terms, of the molar content of alkyl groups that fall withina C_(x-y) range (“M_(x-y)”) to the molar content of the alkyl groupsthat fall within the C₁₀₊ range (“M₁₀₊”): S_(x-y)=M_(x-y)/M₁₀₊×100%,where both M_(x-y) and M₁₀₊ are measured for the mixture as a whole. Ifany reference range other than C₁₀₊ is used to describe a quat mixture(e.g., C_(X-Y) range), the substitution content of the mixture(abbreviated in the exemplified mixtures as “S_(x-y/X-Y)”) and is theratio of the molar content of alkyl groups that fall within a specifiedC_(x-y) range (“M_(x-y)”) to the molar content of the alkyl groups thatfall within the C_(X-Y) reference range (“M_(X-Y)”):S_(x-y/X-Y)=M_(x-y)/M_(X-Y)×100%.

To illustrate, consider the mixture M1 that contains a single moleculeof dialkyl quat A1 and a single molecule of different dialkylimmidazoline quat A2. By definition, each of dialkyl quats A1 and A2 hastwo C₁₀₊ alkyl groups. Suppose, the molecule of quat A1 has one C₂₀alkyl group and one C₁₂ alkyl group, and the molecule of quat A2 has twoC₂₀ alkyl groups. Suppose also, the mixture M1 is to be characterized interms of its C₁₆₋₃₀ substitution content (S₁₆₋₃₀(M1)), e.g., thenarrower, specified range is C₁₆₋₃₀ and the broader, reference range isC₁₀₊.

The C₁₆₋₃₀ substitution content of the mixture M1 can be calculated as:S₁₆₋₃₀(M1)=M₁₆₋₃₀(M1)/M₁₀₊(M1)×100%, where M₁₆₋₃₀ is the C₁₆₋₃₀ molarcontent of the mixture M1 and M₁₀₊(M1) is the C₁₀₊ molar content of themixture M1. Since the molar concentrations of quats A1 and A2 in themixture M1 are identical (one molecule each), the relative molarconcentration may be disregarded, and the absolute numbers of alkylgroups falling within each range may be used instead. Thus, the C₁₆₋₃₀substitution content of the mixture M1 as a whole may be calculated as:S₁₆₋₃₀(M1)=N₁₆₋₃₀(M1)/N₁₀₊(M1)×100%, where N₁₆₋₃₀(M1) is the number ofalkyl groups in the mixture M1 that fall within the C₁₆₋₃₀ range andN₁₀₊(M1) is the number of alkyl groups in the mixture M1 falling withinthe C₁₀₊ range.

The first step is to calculate the values of N₁₆₋₃₀ and N₁₀₊ for themixture. To determine N₁₆₋₃₀ and N₁₀₊, a substituent group is countedevery time it falls within the C₁₀₊ and C16-30 ranges, respectively, forall molecules in the mixture. The same group may be counted more thanonce. The C₂₀ group falls within both the C₁₆₋₃₀ range and the C₁₀₊range and thus should be counted in calculating both N₁₆₋₃₀(M1) andN₁₀₊(M1), while the C₁₂ group fall only within the C₁₀₊ range andtherefore should be counted only in calculating N₁₀₊(M1). Performing thecalculation for the mixture M1 as a whole, N₁₆₋₃₀ is 3 (one C₂₀ group ofquat A1 and two C₂₀ group of the quat A2) and N₊ is 4 (all four groupsare in the C₁₀₊ range) Therefore, S₁₆₋₃₀ for the mixture M1 is 75%(¾×100%).

For more complex quat mixtures, molar concentrations of quats in themixture are taken into account. A non-limiting example illustratescalculation of substitution content for mixture M2 of dialkyl quats A3,A4, and A5. The mixture M2 is characterized in terms of its C₂₀₋₃₀substitution content (the specified substitution range is C₂₀₋₃₀ and thereference substitution range is C₁₀₊):

TABLE 1* V II III (M₂₀₋₃₀) (N₂₀₋₃₀) (P₂₀₋₃₀) C₂₀₋₃₀ molar VI Number ofC₂₀₋₃₀ contribution (S₂₀₋₃₀) alkyl groups molec- of each quat C₂₀₋₃₀ inthe quat ular ((III) × ((IV)) sub- molecule content and C₂₀₋₃₀ stitutionfalling in for each IV molar content of I the C₂₀₋₃₀ quat (M₀//M₁₀₊)content of the the Quat range ((II)/2) Moles mixture mixture A3 1 (one)0.5 2   1 (0.5 × 2) A4 2 (two) 1 0.75 0.75 (1 × 0.75) A5  0 (none) 00.75   0 (0 × 0.75) M2 3.5 1.75 50% (1.75/3.5) *Column (I) identifiesquat components of the mixture M2. Column (II) indicates how many alkylgroups of each quat molecule fall within the C₂₀₋₃₀ range (note thatdialkyl quats have two groups in the C₁₀₊ range (N₁₀₊ is 2)). Column(IV) provides molar amounts of each quat in the mixture M2 and the totalnumber of quat moles in the mixture M2. Columns (III), (V) and (VI) areexplained below.

To calculate the C₂₀₋₃₀ substitution content (S₂₀₋₃₀) of the mixture M2,the first step is to determine the C₂₀₋₃₀ content the molecule of eachquat based on its chemical structure. Such substitution content isreferred to as C₂₀₋₃₀ “molecular content” and denoted as “P₂₀₋₃₀”. TheC₂₀₋₃₀ molecular content of a quat is determined by dividing the numberof C₂₀-C₃₀ alkyl groups (N₂₀₋₃₀) by the number of C₁₀₊ alkyl groups(N₁₀₊) in molecule of the quat: P₂₀₋₃₀=N₂₀₋₃₀/N₁₀₊.

In the example, the nature of substitution for quats in the mixture isprovided in column (II). The molecule of quat A3 has 1 (one) group thatfalls in the C₂₀₋₃₀ range. The number of groups in the C₁₀₊ range is 2(two) for all dialkyl quats. Thus, the C₂₀₋₃₀ molecular content of quatA3 (P₂₀₋₃₀ (A3)) is ½=0.5. The C₂₀₋₃₀ molecular content values for quatsA3, A4, and A5 are calculated in the same manner by dividing the valuesin column (II) by 2, and are shown in column (III).

Next, the C₂₀₋₃₀ molar contribution of each quat component of themixture (M₂₀₋₃₀) is calculated. For this purpose, each quat's C₂₀₋₃₀molecular content (P₂₀₋₃₀, column (III)) is multiplied by the number ofmoles of the corresponding quat in the mixture (M₀, column (IV)):M₂₀₋₃₀=P₂₀₋₃₀×M₀. The results of the calculations are shown in column(V). In effect, the product of the multiplication is the molar amount ofC₂₀₋₃₀ alkyl groups contributed by each quat component of the mixtureM2.

The C₂₀₋₃₀ molar content of the mixture M2 as a whole (M₂₀₋₃₀(M2)) isthe sum of the C₂₀₋₃₀ molar contributions of individual quats:M₂₀₋₃₀(M2)=M₂₀₋₃₀(A3)+M20-30(A4)+M₂₀₋₃₀(A5). Referring to column (V),quat A3 contributes 1 mole of C₂₀-C₃₀ groups (M₂₀₋₃₀(A3)=1), quat A4contributes 0.75 moles (M₂₀₋₃₀(A4)=0.75), and quat A5 contributes 0moles of C₂₀-C₃₀ groups (M₂₀₋₃₀(A5)=0). Therefore, the C₂₀₋₃₀ molarcontent of the mixture M2 is 1.75 (M₂₀₋₃₀(M2)=1+0.75+0).

The sum of the C₁₀₊ molar contributions of individual quats is the C₁₀₊molar content of the mixture M2 as a whole (M₁₀₊(M2)):M₊(M2)=M_(10+(A)3)+M₊(A4)+M_(10+(A)5). Since all dialkyl quats have twoalkyl groups in the C₁₀₊ range, the C₁₀₊ molar content (M₁₀₊) of adialkyl quat component is identical to the number of moles of the quatcomponent (M₀). Referring to column (IV), quat A3 contributes 2 mole ofC₁₀₊ groups (M₀₊(A3)=2), quat A4 contributes 0.75 moles (M₀₊(A4)=0.75),and quat A5 contributes 0.75 moles of C₁₀₊ groups (M₁₀₊(A5)=0.75).Therefore, the C₁₀₊ molar content of the mixture M2 is 3.5(M₁₀₊(M2)=2+0.75+0.75). Finally, the C₂₀₋₃₀ substitution content of themixture M2 can be calculated:S₂₀₋₃₀(M2)=M₂₀₋₃₀(M2)/M₁₀₊(M2)=1.75/3.5=50% (column (VI)).

Another non-limiting example illustrates calculation of the substitutioncontent for mixtures of monoalkyl quats. Table 2 shows mixture M3 ofmonoalkyl quats B1, B2, and B3. The mixture M3 is characterized in termsof its C₂₀₋₂₄ substitution content (the specified substitution range isC₂₀₋₂₄ and the reference substitution range is C₁₀₊).

TABLE 2 II III V VI (N₂₀₋₂₄) (P₂₀₋₂₄) (M₂₀₋₂₄) (S₂₀₋₂₄) Number of C₂₀₋₂₄C₂₀₋₂₄ molar C₂₀₋₂₄ alkyl groups molec- contribution sub- (the C₂₀₋₂₄ular of each quat stitution range) that content (III × IV) and contentof fall in the for each IV C₂₀₋₂₄ molar the I quat quat (M₀//M₁₀₊)content the mixture Quat molecule (II/l) Moles mixture (V/IV) B1 1 1 1.51.5 (1 × 1.5) B2 1 1 1 1 (1 × 1) B3 0 0 2.5   0 (0 × 2.5) M3 5 2.5 2.5/5× 100% = 50%

The C₂₀₋₂₄ substitution content of the mixture M3 (S₂₀₋₂₄ (M3)) iscalculated as follows similarly to the calculations described inreference to the mixture of Table 1:

1. Determine the C₂₀₋₂₄ molecular content for each monoalkyl quat:P₂₀₋₂₄=N₂₀₋₂₄/N₁₀₊. Since N₁₀₊ is 1 (one) for all monoalkyl quats, theC₂₀₋₂₄ molecular content for each quat is calculated as:P₂₀₋₂₄=N₂₀₋₂₄/1. The results are shown in column (III). It is evidentthat P_(x-y)=N_(x-y) for monoalkyl quats in general. Thus, N_(x-y) maybe used instead of P_(x-y) and column (III) is omitted in later examplesof monoalkyl quat mixtures.

2. Determine the C₂₀₋₂₄ molar contributions of quat components bymultiplying the number of C₂₀-C₂₄ groups by molar amount for each quatcomponent: M₂₀₋₂₄=N₂₀₋₂₄×M₀. The N₂₀₋₂₄ values in column (II) aremultiplied by the corresponding M₀ values in column (IV). The results ofthe calculations are in column (V).

3. Determine the C₂₀₋₂₄ molar content of the mixture M3 by adding theC₂₀₋₂₄ molar contributions of the quat components:M₂₀₋₂₄(M3)=M₂₀₋₂₄(B1)+M₂₀₋₂₄(B2)+M₂₀₋₂₄(B3). The M₂₀₋₂₄ values for eachquat component in column (V) are added. The calculated C₂₀₋₂₄ molarcontent of the mixture M3 is also shown in column (V).

4. Determine the C₁₀₊ molar content of the mixture M3 by adding the C₁₀₊molar contributions of the quat components. Since all monoalkyl quatshave one alkyl group in the C₁₀₊ range, molar amounts of the quats areused: M₁₀₊(M3)=M₀(B1)+M₀(B2)+M₀(B3). The M₀ values for each quatcomponent in column (IV) are added. The calculated C₁₀₊ molar content ofthe mixture M3 is shown in column (IV).

5. Determine the C₂₀₋₂₄ substitution content of the mixture M3 bydividing the C₂₀₋₂₄ molar content of the mixture M3 by the C₁₀₊ molarcontent of the quats in the mixture: S₂₀₋₂₄(M3)=M₂₀₋₂₄(M3)/M₁₀₊ (M3) Thecalculated C₂₀₋₂₄ substitution content of the mixture M3 is shown incolumn (VI).

The above definitions and calculation methodologies are used throughoutto describe various aspects and embodiments of the invention.

As described above, quats are useful as active ingredients in hairconditioning products. Their use in such products is related to primarypurpose of product formulation (e.g., conditioning hair). Such primarypurpose(s) of a product and the effectiveness of quats in effecting thispurpose are referred to herein as “primary product performance.” Forexample, in hair conditioning products, primary product performance ofquats is related to their effectiveness in disentangling and/orsoftening hair, etc. Likewise, in shampoos, primary product performanceis related to cleansing effectiveness.

The primary product performance of quats may be, and often is, unrelatedto their effectiveness in forming and/or stabilizing emulations. It isbelieved that for many cosmetic and personal care products, the goals ofprimary product performance and emulsion formation, stability, andappearance are not entirely compatible. For example, conditioning orcleansing performance of a hair care product often depends on the natureand the concentration of quat(s) included in the product. However, thenature and concentrations of quats selected on the basis of theirprimary product performance may not be optimal, or even acceptable, forobtaining and/or stabilizing an emulsion.

For example, it has been discovered that dialkyl quats havinglonger-chain (e.g., C₂₀₊) alkyl groups have improved performance in anumber of personal care applications, such as hair conditioningproducts. At the same time, the presence of such quats with longer-chainalkyl groups tend to make emulsification more difficult and/or mayadversely affect the stability of the emulsion. Without being limited toany specific theory, it is thought that an increase in the length ofalkyl chains of a quat leads to an increase in the lipophilic characterof the quat. As the length of the alkyl chain grows, the balance betweenlipophilisity and hydrophilicity of the quat molecule may shift sosignificantly that formulating emulsions may become difficult.

Even with shorter-chain dialkyl quats, for example, C₁₄-C₁₆ dialkylquats, emulsification often requires presence of a separate emulsifier.However, the traditionally used, non-quat emulsifiers rarely contributeto the primary product performance, and each added ingredientcomplicates product formulation.

The following non-limiting example is helpful. A prior art hairconditioning composition could, for example, include 30% of dialkylimmidazoline quat of the formula (1), where R′ and R′″ are —C₁₅H₂₉. Thiscompound may act both as an emulsifier and an active hair-conditioningingredient. If C₁₅H₂₉ groups are replaced with C₂₂H₄₃, the hairconditioning performance of the composition may improve, but theaddition of a non-quat emulsifying compound(s) may be necessary.However, as described above, such non-quat emulsifiers rarely contributeto hair conditioning performance. Nevertheless, to accommodate theaddition of the emulsifier, the quat content may have to be reduced fromthe amount desired, further affecting the primary product performancethat was the reason for chain length increase in the first place. Forthis reason, the chain length of dialkyl quats was typically kept in theC₁₄-C₁₈ range.

However, it has now been surprisingly discovered that monoalkyl quatsmay be used instead of non-quat emulsifiers in combination with dialkylquats, allowing the use of dialkyl quats with longer alkyl chains. Themonoalkyl quats both contribute to primary product performance (or atleast don't detract from same) and emulsification at the same time,facilitating the balance between performance and emulsification.

Thus, in one embodiment, the present invention provides a compositionthat includes at least two components, wherein the first component isselected for primary product performance, and the second component isselected for its contribution to proper emulsification of the product,but wherein the second component essentially does not detract fromprimary product performance. Preferably, the first component is selectedin such a manner that its use in a product would require addition ofexternal emulsifiers or use of other emulsification techniques, methods,or substances to allow the use of the first component in formulating theproduct as an emulsion. Also, the primary product performance of thefirst component is preferably superior to the primary productperformance of the second component.

In the preferred embodiment, the first component includes one or moredialkyl quats, and the second component includes one or more monoalkylquats. In accordance with a preferred aspect and this embodiment, theinvention provides compositions that include at least:

(a) one or more dialkyl quats in the amount of from about 10% to about90% by weight; and

(b) one or more monoalkyl quats in the amount of from about 90% to about10% by weight; where the percentages are with respect to the sum of theweights of the components (a) and (b).

Preferably, the component (a) is included in the amount of from about20% to about 80%, more preferably, from about 40% to about 70% byweight, and the component (b) in the amount of from about 80% to about20%, more preferably, from about 30% to about 60% by weight.

Below, various dialkyl and monoalkyl quats and their mixtures aredescribed in greater details. It should be understood that anycombination of components (a) and (b) are contemplated.

Component (a)

The component (a) may include dialkyl quats of various chemicalstructures, such as dialkyl immidazoline quats, dialkyl ammonium quats,dialkyl amidoamine quats, and others. The component (a) may contain asingle dialkyl quat, a mixture of quats of the same general structurewith different substitution, or a mixture of different dialkyl quats.

In one embodiment, the dialkyl immidazoline quat is wherein at least aportion of the mixture includes at least one dialkyl immidazoline quathaving at least one C₂₀-C₂₄ alkyl group; the C₂₀₋₂₄ substitution contentof said mixture being from about 10% to about 95% with respect to C₁₀₊reference substitution range.

The preferred dialkyl quats are immidazoline quats. In one embodiment,the component (a) may include one or more dialkyl immidazoline quats ofthe formula (I):

where X is a salt-forming anion, such as chloride, bromide, iodide,fluoride, sulfate, methyl sulfate, methanebenzylsulfonate, phosphate,nitrite, nitrate, carboxylate, or a mixture thereof, preferably,chloride or methyl sulfate; a is the ionic charge of X;

R¹, R², and R³ are independently hydrogen, C₁-C₃₀ alkyl, C₁-C₃₀alkylhydroxy, C₁-C₃₀ alkyl amido R_((C1-C6)) wherein R_((C1-C6)) is aC₁-C₆ alkylene or benzyl, C₁-C₃₀ alkylaryl amido R_((C1-C6)), or C₁-C₃₀alkylhydroxy amido R_((C1-C6));

two of R¹, R², and R³ are independently C₁₀-C₃₀ alkyl, C₁₀-C₃₀alkylhydroxy, C₁₀-C₃₀ alkyl amido R_((C1-C6)), C₁₀-C₃₀ alkylaryl amidoR_((C1-6)), or C₁₀-C₃₀ alkylhydroxy amido R_((C1-C6));

the remaining one of R1, R² and R³ is hydrogen, C₁-C₈ alkyl, C₁--C₈alkylhydroxy, C₁-C₈ alkyl amido R_((C1-C6)), C₁-C₈ alkylaryl amidoR_((C1-C6)), or C₁--C₈ alkylhydroxy amido R_((C1-C6));

R⁴, R⁵, R⁶, and R⁷, same or different, are independently hydrogen,alkyl, arylalkyl, alkylaryl, halogen, including bromo and chloro,acetoxy, alkylacetoxy, arylacetoxy, carboxy, alkylcarboxy, hydroxy, oralkoxyhydroxy, preferably, R⁴, R⁵, R6, and R⁷, same or different, arehydrogen or C₁-C₈ alkyl.

Preferably, R¹ is C₁₀-C₃₀ alkyl or alkylhydroxy, more preferably,C₁₄-C₃₀ alkyl or alkylhydroxy, yet more preferably, C₁₆-C₃₀ alkyl oralkylhydroxy, yet more preferably, C₂₀-C₃₀ alkyl or alkylhydroxy;

R² is C₁-C₆ alkyl, more preferably, C₁-C₃ alkyl, yet more preferably,methyl.

R³ is C₁₀-C₃₀ alkyl amido R_((C1-C6)), more preferably, C₁₄-C₃₀ alkylamido C₁-C₆ alkylene, yet more preferably, C₁₆-C₃₀ alkyl amido C₁-C₃alkylene, yet more preferably, C₂₀-C₃₀ alkyl amido C₁-C₃ alkylene.

The component (a) may contain a single dialkyl immidazoline quat of theformula (I), or a mixture of quats. If the component (a) includes amixture of the compounds of the formula (I), the mixture may have adefined substituion content.

In one preferred embodiment, the component (a) is a mixture of dialkylimmidazoline quats of the formula (I), wherein the percentage ofC₁₆-C₃₀, preferably, C₂₀-C₃₀ groups with respect to the total number ofC₁₀₊ groups in the mixture of the component (a) varies from about 10% toabout 80%, preferably, from about 15% to about 70%, more preferably,from about 20% to about 65%, yet more preferably, from about 35% toabout 60%.

The compounds (1)-(4) are non-limiting examples of the dialkyl quats ofthe formula (I):

In another non-limiting example, Table 3 shows mixture M4 of dialkylquats (1), (2), (3), and (4)and thecalculation of the mixture'ssubstitution content. The mixture M4 is characterized in terms of itsC₂₀₋₃₀ substitution content (the specified substitution range is C₂₀₋₃₀and the reference substitution range is C₁₀₊).

TABLE 3* III V VI II (P₂₀₋₃₀ = IV (M₂₀₋₃₀ = (S₂₀₋₃₀ = I (N₂₀₋₃₀) II/2)(M₀//M₁₀₊) III × IV) V/IV) 1 1 0.5 1 0.5 (0.5 × 1) 2 2 1 2 2 (1 × 2) 3 21 2 2 (1 × 2) 4 1 0.5 3 1.5 (0.5 × 3) M4 8 6 75% (6/8 × 100%)*Explanations for calculating the C₂₀₋₃₀ content are provided withreference to Table 1.

In another embodiment, the component (a) includes or more dialkylimmidazoline quats of the formula (II):

where X and a are as defined above with reference to the formula (I);

n varies from 1 to 3, preferably, n is 2;

m is 1 or 2, preferably, m is 2;

R⁸ and R¹¹, same or different, are C₁₆-C₃₀ alkyl, preferably, C₁₆-C₂₆alkyl, more preferably, C₁₆-C₂₄ alkyl, yet more preferably, C₂₀-C₂₄alkyl;

R⁹ is hydrogen or C₁-C₃ alkyl, preferably, methyl;

R¹⁰ is hydrogen, alkyl, arylalkyl, alkylaryl, halogen, including bromoand chloro, acetoxy, alkylacetoxy, arylacetoxy, carboxy, alkylcarboxy,hydroxy, or alkoxyhydroxy, preferably, hydrogen or lower alkyl, morepreferably, hydrogen.

The particularly preferred compounds of this embodiment have the formula(III):

where X is as defined above; R¹² and R¹⁴, same or different, are C₁₆-C₂₆alkyl, preferably, C₂₀-C₂₄ alkyl; and R¹³ is C₁-C₃ alkyl, preferably,methyl.

The compounds (5)-(8) are examples of dialkyl quats of the formula (II):

Other non-limiting examples of the quats of the formula (II) are quats(9)-(16) shown in Table 4:

TABLE 4* Compound R⁸ R¹¹ 9 C₁₈H₃₅ C₁₈H₃₅ 10 C₂₁H₄₀ C₂₁H₄₀ 11 C₂₂H₄₀C₂₂H₄₀ 12 C₁₆H₂₉ C₁₈H₃₅ 13 C₂₃H₄₀ C₂₃H₄ 14 C₁₈H₃₅ C₂₂H₄₁ 15 C₁₈H₃₃C₁₈H₃₃ 16 C₂₂H₄₀ C₂₂H₄₀ *R⁹ is methyl, R¹⁰ is hydrogen, m is 2, and n is2.

In a non-limiting example, Table 5 shows mixture M5 of dialkyl quats(9), (10), and (11) and the calculation of the mixture's substitutioncontent. The mixture M5 is characterized in terms of its C_(20-24/16-30)substitution content specified range is C₂₀₋₂₄ and the reference rangeis C₁₆₋₃₀). The C₁₆₋₃₀ range is used as the reference range, instead ofthe default C₁₀₊ reference range, since R⁸ and R¹¹ are C₁₆-C₃₀ alkylgroups. The combined molar content of R⁸ and R¹¹ groups in the mixtureM5 is used in the calculations:

TABLE 5 III IV V VI I II (P₂₀₋₂₄ = (M₀// (M₂₀₋₂₄ = III ×(S_(20-24/16-30) = (Quat) (N₂₀₋₂₄) II/2) M₁₀₊) IV) V/IV)  9 0 0 1 0 (0× 1) 10 2 1 0.75 0.75 (0.75 × 1) 11 2 1 0.25 0.25 (0.25 × 1) M5 2 1 50%(1/2 × 100%)

Other non-limiting examples of quat mixtures and calculations of theirC₂₀₋₂₄ content are shown in Tables 6 and 7:

TABLE 6 III IV V VI I II (P₂₀₋₂₄ = (M₀// (M₂₀₋₂₄ = (S_(20-24/16-30) =(Quat) (N₂₀₋₂₄) II/2) M₁₀₊) III × IV) V/IV) 12 0 0 1 0 (0 × 1) 13 2 12.5 2.5 (1 × 2.5) M6 3.5 2.5 71.4% (2.5/3.5 × 100%)

TABLE 7 III V VI I II (P₂₀₋₂₄ = IV (M₂₀₋₂₄ = (S_(20-24/16-30) = (Quat)(N₂₀₋₂₄) II/2) (M₀//M₁₀₊) III × IV) V/IV) 14 1 0.5 2 1 (0.5 × 2) 15 0 01 0 (0 × 1)   16 2 1 1 1 (1 × 1)   M7 4 2 50% (2/4 × 100%)

The component (a) may also include other dialkyl quats, for example,dialkyl amidoamine quats described in U.S. patent application Ser. No.09/409,203, assigned to Croda Incorporated, and incorporated herein byreference herein in its entirety, or dialkyl ammonium quats described inU.S. patent application Ser. No. 09/438,631, also assigned to CrodaIncorporated, and incorporated herein by reference herein in itsentirety.

Examples of suitable dialkyl ammonium quats are ditallow dimethylammonium chloride, dicetyl ammonium chloride, dicetyl ammonium bromide,dilauryl ammonium chloride, dilauryl ammonium bromide, distearylammonium chloride, distearyl ammonium bromide, dicetyl methyl ammoniumchloride, dicetyl methyl ammonium bromide, dilauryl methyl ammoniumchloride, dilauryl methyl ammonium bromide, distearyl methyl ammoniumchloride, distearyl dimethyl ammonium chloride, distearyl methylammonium bromide, and mixtures thereof.

Other dialkyl ammonium quats include those wherein the C₁₂-C₂₂ alkyl isderived from a tallow fatty acid or from a coconut fatty acid. Examplesof such ammonium quats include ditallow dimethyl ammonium chloride,ditallow dimethyl ammonium methyl sulfate, di(hydrogenated tallow)dimethyl ammonium chloride, di(hydrogenated tallow) dimethyl ammoniumacetate, ditallow dipropyl ammonium phosphate, ditallow dimethylammonium nitrate, di(coconutalkyl)dimethyl ammonium chloride,di(coconutalkyl)dimethyl ammonium bromide, dilauryl dimethyl ammoniumchloride, distearyl dimethyl ammonium chloride, dimyristyl dimethylammonium chloride, dipalmityl dimethyl ammonium chloride, distearyldimethyl ammonium chloride, and mixtures thereof.

The dialkyl immidazoline quats of the component (a) may be prepared in anumber of ways, including methods known to those skilled in the art.Thus, one of suitable preparation methods is described in U.S. Pat. No.4,855,440, incorporated herein by reference in its entirety. A possiblesynthetic route involves a reaction of a carboxylic acid, anhydride, ornatural or synthetic oil, with a desired dialkyltriamine, followed byquaternization of the resulting immidazoline intermediate.

Reaction Scheme 1 shows an example of the synthetic route forpreparation of certain dialkyl immidazoline quats, specifically,1-methyl-1-(alkyl-acylamido-) ethyl)-2-alkyl immidazolinium methylsulfates, via a reaction between one mole of diethylene triamine and twomoles of a fatty carboxylic acid (or acids), followed by aquaternization with dimethyl sulfate:

By varying the starting materials and the reactants, various dialkylimmidazoline quats may be obtained. For example, the carboxylic acidsR′COOH and R″COOH may be same or different and may contain a variety ofgroups R′ and R″. The nature of R′ and R″ substitution in the carboxylicacids may be used to vary the R′ and R″ substituents in the resultingdialkyl immidazoline compounds.

The carboxylic groups R′CO— and R″ CO— may be derived from a variety ofsources. The carboxylic groups R′CO— and R″CO— may be derived from avariety of sources. Thus, essentially pure carboxylic acids may be used.The suitable carboxylic acids having C₁₈-C₂₄ alkyl groups include, forexample, arachidic (C²⁰, including the carboxylic carbon¹,

¹Subscripts with reference to the number of carbon atoms indicate thenumber of carbon atoms without the carboxylic group carbon; thesuperscripts indicate the number of carbon atoms of the carboxylic groupincluding the carboxylic carbon. Thus, C²⁰ is C₁₉COO—. and 0 doublebonds in the alkyl group (C²⁰:0)), erucic (C²²:1), behemic (C²²:0),gadoleic (C²⁰:1), erucic (C²²:1), arachadonic (C²:4), culpodonic (C²²:5)eicosapentaenoic (C²⁰:5), docosahexaenoic acid (C²²:6), tetrcosanoic(C²⁴:0); and nervonic (C²⁴:1). Other carboxylic acids, including acidshaving any desirable alkyl substitution may also be used.

¹ Subscripts with reference to the number of carbon atoms indicate thenumber of carbon atoms without the carboxylic group carbon; thesuperscripts indicate the number of carbon atoms of the carboxylic groupincluding the carboxylic carbon. Thus, C²⁰ is C₁₉COO

Also, mixtures of carboxylic acids may be used. If a mixture ofcarboxylic acids is used, the reaction usually provides a correspondingmixture of compounds with R′/R″ substitution content similar oridentical to the R′/R″ distribution in the mixture.

Usually, the use of mixtures of pure carboxylic acids is noteconomically feasible. Rather, the mixtures of carboxylic acids derivedfrom a single source containing various carboxylic groups, such asnatural or synthetic oils, triglycerides, and the like, are typicallyused. For example, such mixtures may be obtained in commercialquantities via saponification of ester-containing natural or syntheticsubstances.

In fact, carboxylic acids may be directly replaced in the reactionsabove by ester-containing natural or synthetic oil or a similarsubstance. Similarly to the use of carboxylic acid mixtures, thereaction between the ester-containing oil and a triamine usuallyprovides a mixture of compounds with R′/R″ substitution content similaror identical to the R′/R″ distribution in the oil.

Preferably, the component (a) contains compounds derived from naturaland synthetic oils, fatty acids and/or triglycerides.

Thus, the component (a) of the composition of the invention may includea product(s) of a reaction between

a compound of the formula

where R′ is C₁-C₁₀ alkylene, preferably —CH₂CH₂— group, and R″ is C₁-C₁₀alkylene, preferably, —CH₂CH₂— alkylene; and

a mixture of natural or synthetic oil-derived carboxylic acids or anatural or synthetic oil.

The suitable oils that may be used directly or provide oil-derivedmixtures of carboxylic acids include, for example, HEAR oil, cod liveroil, herring oil, menhaden oil, mustard seed oil, pilchard oil, hearoil, salmon oil, sardine oil and shark liver oil. Of course, other oilsand similar substances may also be used. For listing of such substances,please see 1 “Bailey's Industrial Oil and Fat Products” (Daniel Swern,John Wiley & Sons, 4th Ed. 1979), at pages 416-417, 447, 449-450, and452, which are hereby incorporated by reference.

Table 8 shows approximate percentages of some of the C²⁰+ (including thecarboxylic carbon) components in some of the common oils:

TABLE 8 Substance C²⁰:0 C²⁰:1 C²⁰:4 C²⁰:5 C²²:0 C²²:1 C²²:5 C²²:6 C²⁴:0Cod liver 8.8-14.6% 2.6-9%   4.6-13.3% 1-2% 8.6-19% oil Herring1.5-19.2% 4.6-10.2% 2.8-19.9%   1-3.7%   3.8-24.1% oil Menhaden0.9-2.7%  0.6-1.2% 10.2-13.5%  0.7-1.7%  1.1-2.3% 3.3-14% oil Pilchard3.2% 1.6% 16.9%  3.6% 2.5% 12.9% (Sardine) oil HEAR oil 0.8-13.5%20.1-59.4%  0.1-1.4% Mustard 7%   44.2% Seed oil

The oils shown in Table 7 generally contain from about 30% to about 90%of C₂₀-C₃₀ alkyl groups in their fatty carboxylic groups. The oils oftenexhibit substantial variations in C₂₀-C₃₀ content, and also include someC₁-C₁₉ alkyl content.

The particularly preferred oil is HEAR oil, especially high erucicrapeseed oil, which typically contains 46% of C²²:1 alkyl (erucic), 1.5%of C²²:0 alkyl (behemic), and 11% of C²⁰:1 alkyl (gadoleic) by weight.

Component (b)

The component (b) may include monoalkyl quats of various chemicalstructures, such as monoalkyl immidazoline quats, monoalkyl ammoniumquats, monoalkyl amidoamine quats, and others. The component (b) maycontain a single monoalkyl quat, a mixture of quats of the same generalstructure with different substitution, or a mixture of differentmonoalkyl quats.

The preferred quats are monoalkyl immidazoline quats and monoalkylammonium quats. The most preferred quats are monoalkyl immidazolinequats. In one embodiment, the component (b) may include one or moremonoalkyl immidazoline quats of the formula (IV):

where X is a salt-forming anion, such as chloride, bromide, iodide,fluoride, sulfate, methyl sulfate, methanebenzylsulfonate, phosphate,nitrite, nitrate, carboxylate, or a mixture thereof, preferably,chloride or methyl sulfate; a is the ionic charge of X;

R¹⁵, R¹⁶ and R¹⁷ are independently hydrogen, C₁-C₃₀ alkyl, C₁-C₃₀alkylhydroxy, C₁-C₃₀ alkyl amido R_(C1-C6), C₁-C₃₀ alkylaryl amidoR_(C1-)C₆, or C₁-C₃₀ alkylhydroxy amido R_(C1-C6), wherein R_(C1-C6) isa C₁-C₆ alkylene or benzyl;

one of R¹⁵, R¹⁶ and R¹⁷ is independently C₁-C₃₀ alkyl, C₁₀-C₃₀alkylhydroxy, C₁₀-C₃₀ alkyl amido R_(C1-C6), C₁₀-C₃₀ alkylaryl amidoR_(C1-)C₆, or C₁₀-C₃₀ alkylhydroxy amido R_(C1-C6);

the remaining two of R¹⁵, R¹⁶ and R¹⁷ are independently hydrogen, C₁-C₈alkyl, C₁-C₈ alkylhydroxy, C₁-C₈ alkyl amido R_(C1-C6), C₁-C₈ alkylarylamido R_(C1)-C₆, or C₁-C₈ alkylhydroxy amido R_(C1-C6);

preferably, R¹⁵ is C₁₀-C₃₀ alkyl or alkylhydroxy, more preferably,C₁₄-C₃₀ alkyl or alkylhydroxy, yet more preferably, R¹⁵ is C₁₆-C₃₀ alkylor alkylhydroxy, yet more preferably, R¹⁵ is C₂₀-C₃₀ alkyl oralkylhydroxy;

R¹⁶ is C₁-C₆ alkyl, more preferably, C₁-C₃ alkyl, yet more preferably,methyl;

R¹⁷ is C₁-C₈ alkyl, C₁-C₈ alkylhydroxy, C₁-C₈ alkyl amido R_(C1-C6), orC₁-C₈ alkylhydroxy amido R_(C1-C6), more preferably, C₁-C₈ alkyl amidoC₁-C₃ alkylene or C₁-C₈ alkylhydroxy;

R¹⁸, R¹⁹, R²⁰, and R²¹, same or different, are independently hydrogen,alkyl, arylalkyl, alkylaryl, halogen, including bromo and chloro,acetoxy, alkylacetoxy, arylacetoxy, carboxy, alkylcarboxy, hydroxy, oralkoxyhydroxy; preferably, R¹⁸, R¹⁹, R²⁰, and R²¹, same or different,are hydrogen or C₁-C₈ alkyl.

Compounds (17)-(19) are non-limiting examples of monoalkyl quats of theformula (IV):

The component (b) may include a single compound of the formula (IV), ora mixture of such compounds. If the component (b) includes a mixture ofthe compounds of the formula (IV), the mixture may have a definedsubstitution content. As described in. reference to dialkyl quats of thecomponent (a), the substitution content of the mixtures is measured as apercentage ratio of a total number of substituents within a specifiedrange to a total number of substituents within a broader referencerange.

The component (b) may be a mixture of monoalkyl immidazoline quats, atleast one of which has a C₁₆-C₃₀ alkyl group; the C₁₆₋₃₀ substitutioncontent of the mixture being from about 10% to about 95%, preferably,from about 15% to about 85%, more preferably, from about 20% to about80%, yet more preferably, from about 25% to about 75%.

Other non-limiting examples of monoalkyl quats of the formula (V) arequats (24)-(28) shown in Table 8:

TABLE 8* Quat R²² 24 C₁₈H₃₅ 25 C₂₁H₄₀ 26 C₂₂H₄₁ 27 C₁₈H₃₃ 28 C₂₂H₄₀ *R²³is CH₃; R²⁴ is hydrogen, R²⁵ is CH₃

In non-limiting examples, Tables 9 and 10 show mixtures M8 and M9,respectively, of quats (24)-(28) and the calculations of theirsubstitution content. Both mixtures are characterized in terms of theirC₂₀₋₂₄ content (the specified range is C20-24 and the reference range isC₁₀₊).

TABLE 9* V I II IV (M₂₀₋₂₀ = VI (Quat) (N₂₀₋₂₄) (M₀//M₁₀₊) II × IV)(S₂₀₋₂₄ = V/IV) 24 0 1 0 (0 × 1) 25 1 1.5 1.5 (1 × 1.5) M8 2.5 1.5 60%(1.5/2.5 × 100%) *N₁₀₊ is 1; column (III) is omitted

TABLE 10* V I II IV (M₂₀₋₂₄ = VI (Quat) (N₂₀₋₄ (M₀//M₁₀₊) II × IV)(S₂₀₋₂₄ = V/IV) 26 1 2 2 (1 × 2) 27 0 1 0 (0 × 1) 28 1 1 1 (1 × 1) M9 43 75% (3/4) × 100%

In another embodiment, the component (b) includes one or more monoalkylimmidazoline compounds of the formula (V):

where X and a are as defined above with reference to the formula (IV);

R²² is C₁₆-C₃₀ alkyl, preferably, C₁₆-C₂₆ alkyl, more preferably,C₁₆-C₂₄ alkyl;

R²³ is hydrogen or C₁-C₃ alkyl;

R²⁴ is hydrogen, alkyl, arylalkyl, alkylaryl, halogen, including bromoand chloro, acetoxy, alkylacetoxy, arylacetoxy, carboxy, alkylcarboxy,hydroxy, or alkoxyhydroxy, preferably, hydrogen or lower alkyl, morepreferably, hydrogen;

R²⁵ is C₁-C₈ alkyl or C₁-C₈ alkylhydroxy;

n varies from 1 to 3, preferably, n is 2; and

m is 1 or 2, preferably, m is 2; or

compounds of the formula (VI):

where X and a are as defined above with reference to the formula (IV);

R²⁶ is C₁₆-C₃₀ alkyl, preferably, C₁₆-C₂₆ alkyl, more preferably,C₁₆-C₂₄ alkyl;

R²⁷ is hydrogen or C₁-C₃ alkyl;

R²⁸ are C₁-C₈ alkyl or C₁-C₈ alkylhydroxy;

n varies from 1 to 3, preferably, n is 2; and

m is 1 or 2, preferably, m is 2.

Compounds (20) and (21) are non-limiting examples of monoalkyl quats ofthe formula (V):

Compounds (22) and (23) are non-limiting examples of monoalkyl quats ofthe formula (VI):

The monoalkyl quats may be prepared in a number of ways, includingmethods known to those skilled in the art. For example, the compounds ofthe invention may be prepared via a reaction of a carboxylic acid,anhydride, or natural or synthetic oil, with a desiredN-alkyl-N-alkylamino-diamine, followed by quaternization of theresulting immidazoline intermediate.

Reaction Scheme 2 shows an example of the synthetic route forpreparation of certain monoalkyl immidazoline quats, specifically,1-methyl-1-(lower alkyl)-2-alkyl immidazolinium chlorides, via areaction between N-lower alkyl-N-ethyleneamino diamine and a fattycarboxylic acid(s), followed by a quaternization with methyl chloride:

By varying the starting materials and the reactants, other immidazolinequaternary compounds may be obtained. For example, if R′″ isalkylhydroxy (e.g., —CH₂CH₂CH₂OH), the resulting monoalkyl quat includesan alkylhydroxy group:

Thus, the component (b) of the composition of the invention may includea product(s) of a reaction between

a) a compound of the formula

where R′ is C₁-C₃ alkylene, preferably —CH₂CH₂— group, and R is C₁-C₈alkyl, C₁-C₈ alkylhydroxy, or benzyl; and

b) a mixture of natural or synthetic oil-derived carboxylic acids or anatural or synthetic oil.

The carboxylic group of monoalkyl immidazoline quats may be derived fromany of the sources described with reference to dialkyl immidazolinequats. The preferred source is also HEAR oil.

In another embodiment, the component (b) may include monoalkyl ammoniumquats of the formula

where X and a are as defined above; R²⁹ is C₁₀-C₃₀ alkyl, C₁₀-C₃₀alkylaryl, C₁₀-C₃₀ arylalkyl or C₁₀-C₃₀ alkylhydroxy; and R³⁰, R³¹, andR³², same or different, are independently hydrogen, C₁-C₈ alkyl or C₁-C₈alkylhydroxy.

Examples of monoalkyl ammonium quats include cetyl ammonium chloride,cetyl ammonium bromide, lauryl ammonium chloride, lauryl ammoniumbromide, stearyl ammonium chloride, stearyl ammonium bromide, cetyldimethyl ammonium chloride, cetyl dimethyl ammonium bromide, lauryldimethyl ammonium chloride, lauryl dimethyl ammonium bromide, stearyldimethyl ammonium chloride, stearyl dimethyl ammonium bromide, cetyltrimethyl ammonium chloride, cetyl trimethyl ammonium bromide, lauryltrimethyl ammonium chloride, lauryl trimethyl ammonium bromide, stearyltrimethyl ammonium chloride, stearyl trimethyl ammonium bromide, andlauryl dimethyl ammonium chloride. Yet other suitable ammonium quats arestearamidopropyl PG-dimonium chloride phosphate, stearamidopropylethyldimonium ethosulfate, stearamidopropyl dimethyl (myristyl acetate)ammonium chloride, stearamidopropyl dimethyl cetearyl ammonium tosylate,stearamidopropyl dimethyl ammonium chloride, stearamidopropyl dimethylammonium lactate, and mixtures thereof.

In general, a producer provides raw quats to manufacturers of personalcare and cosmetic products, who formulate them in the final products. Animportant characteristic of raw quats, as well as the final productsthat incorporate them, is the so-called cationic activity, whichmeasures a concentration of positive charges in a substance, product,etc. The cationic activity may be measured by several methods readilyunderstood by those skilled in the art. One such method utilizes astandardized solution of an anionic material, such as sodium laurylsulfate. This material is added to the solution containing the quatuntil full complexation of the quat's cations (the end point) has beenreached. The end point can be measured potentiometrically or by the useof color indicators.

Typical tests involve titrating a sample of the quat, usually dissolvedin a solvent, with the standardized solution of sodium lauryl sulfateuntil the endpoint is reached. As described in the co-pending andco-assigned U.S. patent application Ser. No. 09/438,631, incorporated byreference herein in its entirety, once the endpoint is reached, thecationic activity can be calculated according to the following formula:${\%\quad{cationic}\quad{activity}} = \frac{{mL} \times N \times {MW} \times 100}{{S.{wt}.} \times 1000}$Where: mL=the number of mL of anionic material

-   -   N=the normality of the solution used    -   MW=the molecular weight of the quat being analyzed    -   S.wt.=the sample weight in grams

For additional information regarding the methodology for measuring thecationic activity, see W. Schempp and H. T. Trau, Wochenblatt furPapierfabrikation 19, 1981, pages 726-732, or J. P. Fischer and K. Lohr,Organic Coatings Science Technology, Volume 8, pages 227-249, MarcelDekker, Inc. April 1986), both incorporated herein by reference in theirentirety.

It is desirable to provide raw quats in a concentrated form with highcationic activity, as a solid or semi-solid solution or dispersion.Without wishing to be bound by any specific theory, it is believed thata desired amount of a given quat or mixture of quats to be placed in aformulation may be measured by the cationic activity of the quat rawmaterial. The quat raw materials with high cationic activity permitbetter transportation efficiency since they occupy smaller space whileproviding the same desired quat amounts. It is also desirable to produceraw quats that, in addition to having high cationic activity, providefor ease in commercial handling and storage. For example, the raw quatthat melt at lower temperatures minimize quat decomposition and improveenergy efficiency. For this purpose, it is preferred for the raw quatsto be flakeable or pastillatable.

Thus, in accordance with another aspect, the invention also providescompositions in the form of concentrated, usually solid, solutions orsuspensions of components (a) and (b) in a suitable carrier. Suchcompositions are called herein quats raw materials. The preferredcarrier is a solvent, and the preferred solvents include isopropylalcohol, SDA-40, propylene glycol, butylenes glycol, various fattyalcohols, and mixtures thereof.

Preferably, the quat raw materials of the invention are flakeable orpastillatable solids with high quat cationic activity. The quat cationicactivity is the cationic activity that is attributed to quaternarynitrogen compounds.

The preferred total quat cationic activity of quat raw materials of theinvention is greater than 10%, preferably, greater than 20%, morepreferably, greater than 35%, yet more preferably, greater than 50%.With respect to relative contributions of the components (a) and (b),preferably, the component (a) provides from about 20% to about 90%, andthe component (b) provides from about 10% to about 75%, of the totalquat cationic activity in the raw material. The quat raw materials ofthe invention may also include one or more desirable ingredients offinal cosmetic/personal care formulations, such as emollients and thelike, as well as various impurities. The list of such ingredients may befound below.

In accordance with another aspect, the invention also providescompositions in the form of various cosmetic and/or personal careproducts. In such form, the compositions of the invention includecomponents (a), and (b), and may include various other ingredients, suchas active and additional ingredients, both conventional and otherwise.Such compositions may be referred to as final product compositions, andmay be in the form of, for example, sunscreen compositions for hairand/or skin, such as lotions, gels, sprays, and the like, hand cleaners,bath compositions, suntan oils, anti-perspirant compositions, perfumesand colognes, cold creams, pre-shaves, deodorants, topicalpharmaceutical ointments, skin moisturizers, facial cleansers, cleansingcreams, skin gels, shampoos, hair conditioners, detergents, householdcleaning products, make-up products, lipstick products, mascara, andhair coloring products. The preferred final product compositions of theinvention are compositions for treating human hair, such as shampoos orconditioners.

The final product compositions of the invention, including preparationsfor skin and hair, include components (a), and (b) described herein. Thetotal amount of components (a), and (b) in the products depend on thespecific application, and may vary from about 0.1% to about 40%, morepreferably, from about 0.1% to about 10%, yet more preferably, fromabout 0.5% to about 2% by the weight of the product composition.However, different amounts of quat mixtures may be preferred dependingon the nature of the product.

The final product compositions that include components (a) and (b) maybe in the form of liquids, gels, creams, emulsions, foams, and solids;may be clear or opaque; and may be formulated as aqueous and non-aqueouspreparations, including but not limited to topical preparations.Preferably, the final product compositions are dispersions or solutionsin water, or in a mixture of water with a suitable secondary solvent.Suitable inert solvents include various lower alkanols and glycols.Lower alkanols having from one to four carbon atoms are suitable for usewith the present invention, and lower alkanols having from two to threecarbon atoms are preferred. Glycols having from three to eight carbonatoms are suitable for use with the present invention, while glycolshaving from three to six carbon atoms are preferred. Examples ofsuitable lower alkanols and glycols include methanol, ethanol,isopropanol, butanol, hexylene glycol, 1,3-butylene glycol, 1,2- and1,3-propane diol, 2-methyl 1,3-propane diol, propylene glycol,diethylene glycol, and the like. The total amount of solvent may be upto about 98% by weight of the composition, preferably, from about 20% toabout 90%, more preferably, from about 50% to about 90% by weight of thecomposition. Again, however, different amounts of solvent may bepreferred depending on the nature of the product. If a mixture of waterand a secondary solvent is used, the secondary solvent may be present inthe amount of up to 90%, preferably, between about 25% and about 80% byweight of water in the composition.

It is believed that immidazoline quat and/or quat mixtures improves hairsubstantivity of hydrophobic ingredients of cosmetic and personal careproducts, which is typically thought of as the degree of deposition ofthe hydrophobic ingredient on hair and is desirable. The hydrophobiccomponents are those that are substantially insoluble in water.Typically, such hydrophobic ingredients are soluble in oils. Thus, thecompositions described herein may further include at least onehydrophobic ingredient, examples of which include botanical extracts,vitamin E, vitamin A, silicones, waxes and antioxidants.

In addition to components (a), and (b), the compositions of theinvention may include various active and additional ingredients, bothconventional and otherwise. Of course, a decision to include aningredient and the choice of specific active and additional ingredientsdepends on the specific application and product formulation. Also, theline of demarcation between an “active” ingredient and an “additionalingredient” is artificial and dependent on the specific application andproduct type. A substance that is an “active” ingredient in oneapplication or product may be an “additional” ingredient in another, andvice versa.

Thus, the compositions of the invention may include one or more activeingredients, which provide some benefit to the object of the applicationof the composition, for example, hair or skin. Such active ingredientsmay include one or more substances such as cleaning agents, hairconditioning agents, skin conditioning agents, hair styling agents,antidandruff agents, hair growth promoters, perfumes, sunscreencompounds, pigments, moisturizers, film formers, hair colors, make-upagents, detergents, thickening agents, emulsifiers, antiseptic agents,deodorant actives and surfactants.

The choice of the active ingredient(s) depends on the nature of thedesired cosmetic or personal care product. For example, the sunscreencompounds may be used in the sunscreen lotions, shampoos, hair carelotions and the like. For each type of active ingredient, one or morecompounds may be present. Likewise, more than one type of activeingredient may be present.

Surfactants

In addition to components (a) and (b), other surfactants may be presentin the compositions of the invention, including one or more nonionicsurfactants, anionic surfactants, cationic surfactants, amphotericsurfactants, zwitterionic surfactants, and mixtures thereof. For some ofsurfactants that may be used in combination with the compositions of theinvention, please see McCutcheon's, Detergents and Emulsifiers, (1986),U.S. Pat. Nos. 5,151,210, 5,151,209, 5,120,532, 5,011,681, 4,788,006,4,741,855, U.S. Pat. No. 4,704,272, 4,557,853, 4,421,769, 3,755,560; allincorporated herein by reference in their entirety. The total amounts ofsurfactants in the composition may vary from 1 to 75%, depending on thenature of specific product.

Cationic surfactants

The components (a) and (b) are cationic surfactants suitable for use invarious personal care products, especially hair care products such asconditioners and shampoos. In addition, other cationic surfactants maybe present in the compositions of the invention. The amounts and thenature of cationic surfactants present in the compositions of theinvention depend on the nature of the composition. In the final productcomposition, the total amount of cationic surfactants, including thecomponents (a) and (b) described herein, may vary from 0.1% to about40%, more preferably, from about 0.1% to about 15%, yet more preferably,from about 0.5% to about 2% by the weight of the product composition.However, different amounts of cationic surfactants may be preferreddepending on the nature of the product. Suitable additional cationicsurfactants are disclosed in McCutcheon, Detergents & Emulsifiers, (M.C.Publishing Co. 1979); U.S. Pat. Nos. 3,155,591, 3,929,678, 3,959,461,4,387,090, which are incorporated by reference herein.

Fatty Amines

The compositions of the invention may also include salts of primary,secondary and tertiary C₁₂-C₂₂ amines. Examples of such suitable aminesinclude stearamido propyl dimethyl amine, diethyl amino ethylstearamide, dimethyl stearamine, dimethyl soyamine, soyamine,tri(decyl)amine, ethyl stearylamine, ethoxylated stearylamine,dihydroxyethyl stearylamine, and arachidylbehenylamine. Suitable aminesalts include the halogen, acetate, phosphate, nitrate, citrate, lactateand alkyl sulfate salts. Such salts include stearylamine hydrochloride,soyamine chloride, stearylamine formate, N-tallowpropane diaminedichloride and stearamidopropyl dimethylamine citrate. Some cationicamine surfactants useful in the compositions of the present inventionare disclosed in U.S. Pat. No. 4,275,055, incorporated by referenceherein.

Amidoamines

The compositions of the invention may also include aminoamides, such asdisclosed in U.S. patent application Ser. No. 09/409,203, assigned toCroda Inc., and incorporated by reference herein.

Non-ionic Surfactants

The compositions of the invention may also include various non-ionicsurfactants. Among the suitable nonionic surfactants are condensationproducts of C₈-C₃₀ alcohols with sugar or starch polymers. Thesecompounds can be represented by the formula (S)_(n) —O-R, wherein S is asugar moiety such as glucose, fructose, mannose, and galactose; n is aninteger of from about 1 to about 1000, and R is C₈-C₃₀ alkyl. Examplesof suitable C₈-C₃₀ alcohols from which the R group may be derivedinclude decyl alcohol, cetyl alcohol, stearyl alcohol, lauryl alcohol,myristyl alcohol, oleyl alcohol, and the like. Specific examples ofthese surfactants include decyl polyglucoside and lauryl polyglucoside.

Other suitable nonionic surfactants include the condensation products ofalkylene oxides with fatty acids (i.e., alkylene oxide esters of fattyacids). These materials have the general formula RCO(X)_(n) OH, whereinR is a C₁₀-C₃₀ alkyl, X is —OCH₂CH₂— (derived from ethylene oxide) or—OCH₂CHCH₃— (derived from propylene oxide), and n is an integer fromabout 1 to about 200.

Yet other suitable nonionic surfactants are the condensation products ofalkylene oxides with fatty acids (i.e., alkylene oxide diesters of fattyacids) having the formula RCO(X)_(n)OOCR, wherein R is a C₁₀-C₃₀ alkyl,X is —OCH₂CH₂— (derived from ethylene oxide) or —OCH₂CHCH₃— (derivedfrom propylene oxide), and n is an integer from about 1 to about 200.

Yet other nonionic surfactants are the condensation products of alkyleneoxides with fatty alcohols (i.e., alkylene oxide ethers of fattyalcohols) having the general formula R(X)_(n)OR′, wherein R is C₁₀-C₃₀alkyl, n is an integer from about 1 to about 200, and R′ is H or aC₁₀-C₃₀ alkyl.

Still other nonionic surfactants are the compounds having the formulaRCO(X)_(n)OR′ wherein R and R′ are C₁₀-C₃₀ alkyl, X is —OCH₂CH₂—(derived from ethylene oxide) or —OCH₂CHCH₃— (derived from propyleneoxide), and n is an integer from about 1 to about 200.

Examples of alkylene oxide-derived nonionic surfactants includeceteth-1, ceteth-2, ceteth-6, ceteth-10, ceteth-12, ceteraeth-2,ceteareth6, ceteareth-10, ceteareth-12, steareth-1, steareth-2,stearteth-6, steareth-10, steareth-12, PEG-2 stearate, PEG4 stearate,PEG6 stearate, PEG-10 stearate, PEG-12 stearate, PEG-20 glycerylstearate, PEG-80 glyceryl tallowate, PPG-10 glyceryl stearate, PEG-30glyceryl cocoate, PEG-80 glyceryl cocoate, PEG-200 glyceryl tallowate,PEG-8 dilaurate, PEG-10 distearate, and mixtures thereof.

Still other useful nonionic surfactants include polyhydroxy fatty acidamides disclosed, for example, in U.S. Pat. Nos. 2,965,576, 2,703,798,and 1,985,424, which are incorporated herein by reference.

Anionic Surfactants

The compositions of the invention may also include various anionicsurfactants. Several examples of suitable anionic surfactants aredisclosed in U.S. Pat. No. 3,929,678, which is incorporated herein byreference. Further examples of suitable anionic surfactants includealkoyl isethionates, and alkyl ether sulfates.

The alkoyl isethionates typically have the formula RCO—OCH₂CH₂— SO₃M,wherein R is C₁₀-C₃₀ alkyl, and M is a water-soluble cation, such asammonium, sodium, potassium, or triethanolamine. The examples ofsuitable isethionates include ammonium cocoyl isethionate, sodium cocoylisethionate, sodium lauroyl isethionate, sodium stearoyl isethionate,and mixtures thereof. Preferred for used herein are ammonium cocoylisethionate, sodium cocoyl isethionate, and mixtures thereof.

The alkyl ether sulfates typically have the formulas ROSO₃M andRO(C₂H₄O)_(x)SO₃M, where R is C₁₀-C₃₀ alkyl, x varies from about 1 toabout 10, and M is a water-soluble cation such as ammonium, sodium,potassium and triethanolamine.

Yet another suitable class of anionic surfactants are alkali metal saltsof C₈-C₃₀ carboxylic acids and alkylsulfonates of the formula R₁-SO₃M(where R₁ is C₈-C₃₀ alkyl; preferably, C₁₂-C₂₂ alkyl, and M is acation), including succinamates, and C₁₂-C₂₄ olefin sulfonates andcarboxylates.

Amphoteric Surfactants

The compositions of the invention may also include zwitterionic andamphoteric surfactants. Suitable amphoteric and zwitterionic surfactantsare, for example, derivatives of mono- or di-C₈-C₂₄ secondary andtertiary amines, such as alkyl imino acetates, carboxylates, sulfonates,sulfates, phosphates, and phosphonates, including iminodialkanoates andaminoalkanoates of the formulas RN(CH₂)_(m) CO₂ M₂ and RNH(CH₂)_(m)CO₂M, where m varies from 1 to 4, R is C₈-C₃₀ alkyl; preferably, C₁₂-C₂₂alkyl, and M is H, alkali metal, alkaline earth metal ammonium, oralkanolammonium.

Other suitable amphoteric and zwitterionic surfactants are imidazoliniumand ammonium derivates. Suitable examples of such amphoteric surfactantsinclude sodium 3-dodecyl-aminopropionate, sodium 3-dodecylaminopropanesulfonate, N-alkyltaurines; N-higher alkyl aspartic acids, andcoamidopropyl PG-dimonium chloride phosphate. For further examples ofsuitable amphoteric and zwitterionic surfactants, please see U.S. Pat.Nos. 2,658,072, 2,438,091, and 2,528,378, which are incorporated hereinby reference

Yet other suitable amphoteric and zwitterionic surfactants are betaines.Examples of suitable betaines include coco dimethyl carboxymethylbetaine, lauryl dimethyl carboxymethyl betaine, lauryl dimethylalphacarboxyethyl betaine, cetyl dimethyl carboxymethyl betaine, cetyldimethyl betaine, lauryl bis-(2-hydroxyethyl) carboxymethyl betaine,stearyl bis-(2-hydroxypropyl) carboxymethyl betaine, oleyl dimethylgamma-carboxypropyl betaine, lauryl bis-(2-hydroxypropyl)alpha-carboxyethyl betaine, coco dimethyl sulfopropyl betaine, stearyldimethyl sulfopropyl betaine, lauryl dimethyl sulfoethyl betaine, laurylbis-(2-hydroxyethyl) sulfopropyl betaine, and amidobetaines andamidosulfobetaines, oleyl betaine, and cocamidopropyl betaine.

Sunscreen Compounds

A wide variety of sunscreen compounds are suitable for use with thecompositions of the present invention. Depending on the nature of thecomposition, the sunscreen compounds may be added in the amount of up toabout 40% by weight of the composition, preferably, from about 1% toabout 30%. However, the preferred amount may vary depending on thenature of the composition. Thus, for the final product compositions inthe form of a shampoo or conditioner, the suitable sunscreen agent maybe included in the amount of up to about 40% by weight of thecomposition, preferably, from about 0.5% to about 5%, more preferably,from about 05 to about 1.5% by weight of the composition. Suitablesunscreen compounds include, for example, p-aminobenzoic acid, its saltsand its derivatives; anthranilates; salicylates; cinnamic acidderivatives; dihydroxycinnamic acid derivatives; trihydroxycinnamic acidderivatives; hydrocarbons; dibenzalacetone and benzalacetophenone;naphtholsulfonates; dihydroxy-naphtholic acid and its salts; coumarinderivatives; diazoles; quinine salts; quinoline derivatives; hydroxy- ormethoxy-substituted benzophenones; uric and vilouric acids; tannic acidand its derivatives; hydroquinone; amino benzoates, salicylates,ferrulic acid derivatives, phenylbenzimidazole sulfonic acids,benzophenone sulfonic acids, thioctic acids derivatives, oil-solublecinnamates, and benzophenones. For other suitable sunscreen compounds,please see Segarin, et al., Cosmetics Science and Technology, ChapterVIII, pages 189 et seq., incorporated herein by reference.

Specific suitable sunscreen compounds include 2-ethylhexylp-methoxycinnamate, 4,4′-t-butyl methoxydibenzoylmethane,2-hydroxy-4-methoxybenzophenone, octyldimethyl p-aminobenzoic acid,digalloyltrioleate, 2,2-dihydroxy-4-methoxybenzophenone,ethyl-4->bis(hydroxypropyl)!-aminobenzoate,2-ethylhexyl-2-cyano-3,3-diphenylacrylate, 2-ethylhexylsalicylate,glyceryl p-aminobenzoate, 3,3,5-trimethylcyclohexylsalicylate,methylanthranilate, p-dimethylaminobenzoic acid or aminobenzoate,2-ethylhexyl p-dimethylaminobenzoate, 2-phenylbenzimidazole-5-sulfonicacid, 2-(p-dimethyl-aminophenyl)-5-sulfonicbenzoxazoic acid,paraaminobenzoic acid, benzophenone-1, benzophenone-1, benzophenone-2,benzophenone-3, benzophenone-4, benzophenone-5, benzophenone-6,benzophenone-8, benzophenone-12, methoxycinnamate, avobenzone, ethyldihydroxypropyl para-aminobenzoate, glyceryl para-aminobenzoate, methylanthranilate, octocrylene, octyl dimethyl para-aminobenzoate, octylmethoxycinnamate, octyl salicylate, zinc oxide, titanium dioxide, andred petrolatum.

Emollients

The compositions of the invention may also include one or emollientcompounds such as fats, waxes, lipids, silicones, hydrocarbons, fattyalcohols and a wide variety of solvent materials. The amount of theemollient depends on the application. For the final productcompositions, emmollinets are included in the amount of up to 50% byweight of the composition, preferably, from about 0.1% to about 20%, andmore preferably, from about 0.5% to about 10% by weight of thecomposition.

Examples of suitable emollients include C₈-₃₀ alkyl esters of C₈-₃₀carboxylic acids; C₁₋₆ diol monoesters and diesters of C₈₋₃₀ carboxylicacids; monoglycerides, diglycerides, and triglycerides of C₈₋₃₀carboxylic acids, cholesterol esters of C₈₋₃₀ carboxylic acids,cholesterol, and hydrocarbons. Examples of these materials includediisopropyl adipate, isopropyl myristate, isopropyl palmitate,ethylhexyl palmitate, isodecyl neopentanoate, C₁₂₋₁₅ alcohols benzoates,diethylhexyl maleate, PPG-14 butyl ether, PPG-2 myristyl etherpropionate, cetyl ricinoleate, cholesterol stearate, cholesterolisosterate, cholesterol acetate, jojoba oil, cocoa butter, shea butter,lanolin, lanolin esters, mineral oil, petrolatum, and straight andbranched C₁₆-C₃₀ hydrocarbons.

Also useful are straight and branched chain fatty C₈-C₃₀ alcohols, forexample, stearyl alcohol, isostearyl alcohol, ehenyl alcohol, cetylalcohol, isocetyl alcohol, and mixtures thereof. Examples of othersuitable emollients are disclosed in U.S. Pat. No. 4,919,934; which isincorporated herein by reference in its entirety.

Other suitable emollients are various alkoxylated ethers, diethers,esters, diesters, and trimesters. Examples of suitable alkoxylatedethers include PPG-10 butyl ether, PPG-11 butyl ether, PPG-12 butylether, PPG-13 butyl ether, PPG-14 butyl ether, PPG-15 butyl ether,PPG-16 butyl ether, PPG-17 butyl ether, PPG-18 butyl ether, PPG-19 butylether, PPG-20 butyl ether, PPG-22 butyl ether, PPG-24 butyl ether,PPG-30 butyl ether, PPG-11 stearyl ether, PPG-15 stearyl ether, PPG-10oleyl ether, PPG-7 lauryl ether, PPG-30 isocetyl ether, PPG-10 glycerylether, PPG-15 glyceryl ether, PPG-10 butyleneglycol ether, PPG-15butylene glycol ether, PPG-27 glyceryl ether, PPG-30 cetyl ether, PPG-28cetyl ether, PPG-10 cetyl ether, PPG-10 hexylene glycol ether, PPG-15hexylene glycol ether, PPG-10 1,2,6-hexanetriol ether, PPG-151,2,6-hexanetriol ether, and mixtures thereof.

Examples of alkoxylated diethers include PPG-10 1,4-butanediol diether,PPG-12 1,4-butanediol diether, PPG-14 1,4-butanediol diether, PPG-2butanediol diether, PPG-10 1,6-hexanediol diether, PPG-12 1,6-hexanedioldiether, PPG-14 hexanediol diether, PPG-20 hexanediol diether, andmixtures thereof. Preferred are those selected from the group consistingof PPG-10 1,4-butanediol diether, PPG-12 1,4-butanediol diether, PPG-101,6-hexandiol diether, and PPG-12 hexanediol diether, and mixturesthereof.

Examples of suitable alkoxylated diesters and trimesters are disclosedin U.S. Pat. Nos. 5,382,377, 5,455,025 and 5,597,555, assigned to CrodaInc., and incorporated herein by reference.

Suitable lipids include C₈-C₂₀ alcohol monosorbitan esters, C₈-C₂₀alcohol sorbitan diesters, C₈-C₂₀ alcohol sorbitan triesters, C₈-C₂₀alcohol sucrose monoesters, C₈-C₂₀ alcohol sucrose diesters, C₈-C₂₀alcohol sucrose triesters, and C₈-C₂₀ fatty alcohol esters ofC₂-C₆₂-hydroxy acids. Examples of specific suitable lipids are sorbitandiisostearate, sorbitan dioleate, sorbitan distearate, sorbitanisosotearate, sorbitan laurate, sorbitan oleate, sorbitan palmitate,sorbitan sesquioleate, sorbitan esquistearte, sorbitan stearate,sorbitan triiostearte, sorbitan trioleate, orbitan tristeate, sucrosecocoate, sucrodilaurate, sucrose distearate, sucrose laurate, sucrosemyristate, sucrose oleate, sucrose palmitate, sucrose ricinoleate,sucrose stearate, sucrose tribehenate, sucrose tristearate, myristyllactate, stearyl lactate, isostearyl lactate, cetyl lactate, palmityllactate, cocoyl lactate, and mixtures thereof.

Other suitable emollients include mineral oil, petrolatum, cholesterol,dimethicone, dimethiconol, stearyl alcohol, cetyl alcohol, behenylalcohol, diisopropyl adipate, isopropyl myristate, myristyl myristate,cetyl ricinoleate, sorbitan distearte, sorbitan dilaurate, sorbitanstearate, sorbitan laurate, sucrose laurate, sucrose dilaurate, sodiumisostearyl lactylate, lauryl pidolate, sorbitan stearate, stearylacohol, cetyl alcohol, behenyl alcohol, PPG-14 butyl ether, PPG-15stearyl ether, and mixtures thereof.

Emulsifiers

The compositions of the invention may also include various emulsifiers.In the final product compositions of the invention, emulsifiers may beincluded in the amount of up to about 10%, preferably, in the amount offrom about 0.5% to about 5% by weight of the composition. The examplesof suitable emulsifiers include stearamidopropyl PG-dimonium chloridephosphate, stearamidopropyl ethyldimonium ethosulfate, stearamidopropyldimethyl (myristyl acetate) ammonium chloride, stearamidopropyl dimethylcetearyl ammonium tosylate, stearamidopropyl dimethyl ammonium chloride,stearamidopropyl dimethyl ammonium lactate, polyethyleneglycols,polypropyleneglyocis, and mixtures thereof.

Anti-Dandruff

The compositions of the invention may also include antidandruff agents.The examples of suitable antidandruff agents include zinc pyrithione,sulphur, and selenium sulfide.

Hair Oxidizers

The compositions of the invention may also include hairoxidizing/reducing agents. The examples of suitable hairoxidizing/reducing agents include hydrogen peroxide, perborate,thioglycolates and persulfate salts.

Thickeners

The compositions of the invention may also include various thickeners,such as cross-linked acrylates, nonionic polyacrylamides, xanthan gum,guar gum, gellan gum, and the like; polyalkyl siloxanes, polyarylsiloxanes, and aminosilicones. In the final product compositions of theinvention, thickeners may be included in the amount of up to about 10%,preferably, in the amount of from about 0.2% to about 5% by weight ofthe composition.

The specific examples of the suitable thickening silicon compoundsinclude polydimethylsiloxane, phenylsilicone, polydiethylsiloxane, andpolymethylphenylsiloxane. Some of the suitable silicon compounds aredescribed in European Patent Application EP 95,238 and U.S. Pat. No.4,185,017, which are incorporated herein by reference. The compositionsof the invention may also include silicone polymer materials, whichprovide both style retention and conditioning benefits to the hair. Suchmaterials are described in U.S. Pat. No. 4,902,499, which isincorporated herein by reference.

Hair Conditioning Agents

The compositions of the invention may also include hydrolyzed animalprotein hair conditioning agents. Croda Incorporated sells an example ofa commercially available material under the tradename Crotein Q-RTM.Other examples include urea, glycerol, and propoxylated glycerols,including those described in U.S. Pat. No. 4,976,953, which isincorporated by reference herein.

Hair Setting Agents

The compositions of the invention may also include a hair setting agentto impart styling benefits upon application to hair. The hair settingpolymers may be homopolymers, copolymers, terpolymers, etc. Forconvenience in describing the polymers hereof, monomeric units presentin the polymers may be referred to as the monomers from which they canbe derived. The monomers can be ionic (e.g., anionic, cationic,amphoteric, zwitterionic) or nonionic.

Examples of anionic monomers include unsaturated carboxylic acidmonomers such as acrylic acid, methacrylic acid, maleic acid, maleicacid half ester, itaconic acid, fumaric acid, and crotonic acid; halfesters of an unsaturated polybasic acid anhydride such as succinicanhydride, phthalic anhydride or the like with a hydroxylgroup-containing acrylate and/or methacrylate such as hydroxyethylacrylate and, hydroxyethyl methacrylate, hydroxypropyl acrylate and thelike; monomers having a sulfonic acid group such as styrenesulfonicacid, sulfoethyl acrylate and methacrylate, and the like; and monomershaving a phosphoric acid group such as acid phosphooxyethyl acrylate andmethacrylate, 3-chloro-2-acid phosphooxypropyl acrylate andmethacrylate, and the like.

Examples of cationic monomers include monomers derived from acrylic acidor methacrylic acid, and a quaternarized epihalohydrin product of atrialkylamine having 1 to 5 carbon atoms in the alkyl such as(meth)acryloxypropyltrimethylammonium chloride and(meth)acryloxypropyl-triethylammonium bromide; amine derivatives ofmethacrylic acid or amine derivatives of methacrylamide derived frommethacrylic acid or methacrylamide and a dialkylalkanolamine havingC₁-C₆ alkyl groups such as dimethylaminoethyl (meth)acrylate,diethylaminoethyl (meth)acrylate, dimethylaminopropyl (meth)acrylate, ordimethylaminopropyl (meth)acrylamide.

Examples of the amphoteric monomers include zwitterionized derivativesof the aforementioned amine derivatives of (meth)acrylic acids or theamine derivatives of (meth)acrylamide such as dimethylaminoethyl(meth)acrylate, dimethylaminopropyl(meth)acrylamide by a halogenatedfatty acid salt such as potassium monochloroacetate, sodiummonobromopropionate, aminomethylpropanol salt of monochloroacetic acid,triethanolamine salts of monochloroacetic acid and the like; and aminederivatives of (meth)acrylic acid or (meth)acrylamide, as discussedabove, modified with propanesultone.

Examples of nonionic monomers are acrylic or methacrylic acid esters ofC₁-C₂₄ alcohols, such as methanol, ethanol, 1-propanol, 2-propanol,1-butanol, 2-methyl-1-propanol, 1-pentanol, 2-pentanol, 3-pentanol,2-methyl-1-butanol, 1-methyl-1-butanol, 3-methyl-1-butanol,1-methyl-1-pentanol, 2-methyl-1-pentanol, 3-methyl-1-pentanol,t-butanol, cyclohexanol, 2-ethyl-1-butanol, 3-heptanol, benzyl alcohol,2-octanol, 6-methyl-1-heptanol, 2-ethyl-1-hexanol,3,5-dimethyl-1-hexanol, 3,5,5-trimethyl-1-hexanol, 1-decanol,1-dodecanol, 1-hexadecanol, 1-octadecanol, styrene; chlorostyrene; vinylesters such as vinyl acetate; vinyl chloride; vinylidene chloride;acrylonitrile; alpha-methylstyrene; t-butylstyrene; butadiene;cyclohexadiene; ethylene; propylene; vinyl toluene; alkoxyalkyl(meth)acrylate, methoxy ethyl (meth)acrylate, butoxyethyl(meth)acrylate; allyl acrylate, allyl methacrylate, cyclohexyl acrylateand methacrylate, oleyl acrylate and methacrylate, benzyl acrylate andmethacrylate, tetrahydrofurfuryl acrylate and methacrylate, ethyleneglycol di-acrylate and-methacrylate, 1,3-butyleneglycol di-acrylateand-methacrylate, diacetonacrylamide, isobornyl (meth)acrylate, n-butylmethacrylate, isobutyl methacrylate, 2-ethylhexyl methacrylate, methylmethacrylate, t-butylacrylate, t-butylmethacrylate, and mixturesthereof.

Examples of anionic hair styling polymers are copolymers of vinylacetate and crotonic acid, terpolymers of vinyl acetate, crotonic acidand a vinyl ester of an alpha-branched saturated aliphaticmonocarboxylic acid such as vinyl neodecanoate; and copolymers of methylvinyl ether and maleic anhydride, acrylic copolymers and terpolymerscontaining acrylic acid or methacrylic acid.

Examples of cationic hair styling polymers are copolymers ofamino-functional acrylate monomers such as lower alkylamino alkylacrylate or methacrylate monomers such as dimethylaminoethylmethacrylate with compatible monomers such asN-vinylpyrrolidone or alkyl methacrylates such as methyl methacrylateand ethyl methacrylate and alkyl acrylates such as methyl acrylate andbutyl acrylate.

Miscellaneous Components

The compositions of the invention may also include a wide range ofmiscellaneous ingredients. Some suitable miscellaneous ingredientscommonly used in the cosmetic and personal care industry are describedin The CTFA Cosmetic Ingredient Handbook, (2^(nd) Ed., 1992), which isincorporated by reference herein.

Thus, the compositions of the invention may also include one or moreabsorbents, anti-acne agents, anti-perspirants, anticaking agents,antifoaming agents, antimicrobial agents, antioxidants, antidandruffagents, astringents, binders, buffers, biological additives, bufferingagents, bulking agents, chelating agents, chemical additives, couplingagents, conditioners, colorants, cosmetic astringents, cosmeticbiocides, denaturants, drug astringents, detergents, dispersants,external analgesics, film formers, foaming agents, fragrance components,humectants, keratolytics, opacifying agents, pH adjusters,preservatives, propellants, proteins, retinoids, reducing agents,sequestrants, skin bleaching agents, skin-conditioning agents(humectants, miscellaneous, and occulsive), skin soothing agents, skinhealing agents, softeners, solubilizing agents, lubricants, penetrants,plastisizers, solvents and co-solvents, sunscreening additives, salts,essential oils, and vitamins.

The examples of suitable pH adjusters include sodium hydroxide,triethanoleamine, and aminomethylpropanol, and mixtures thereof. If pHadjusters are present in a final product composition, the amount mayvary from about 0.01% to about 5%, preferably, from about 0.1% to about2% by weight of the composition.

The examples of suitable film formers include glycerin/diethylene glycolmyrystate copolymer, glycerin/diethylene glycol adipate copolymer, ethylester of PVM/MA copolymer,PVP/dimethiconylacrylate/polycarbamyl/polyglycol ester, and mixturesthereof. If the film formers are present in the final productcompositions, the amount may vary from about 0.1% to about 15.0% byweight of the composition, preferably, from about 0.1% to about 2.5% byweight of the composition.

The examples of suitable vitamins include tocopherol, tocopherolacetate, retinoic acid, retinol, and retinoids.

The examples of suitable anti-acne medicaments include resorcinol,sulfur, salicylic acid, erythromycin, zinc, and benzoyl peroxide.

The examples of suitable skin bleaching or lightening agents includehydroquinone, and kojic acid. The examples of suitable aestheticcomponents such as fragrances, pigments, colorings, and the like,include panthenol and derivatives (e.g., ethyl panthenol), aloe vera,pantothenic acid and its derivatives, clove oil, menthol, camphor,eucalyptus oil, eugenol, menthyl lactate, witch hazel distillate,allantoin, bisabolol, and dipotassium glycyrrhizinate.

The compositions of the invention are further illustrated in theexamples that follow.

EXAMPLE 1

Preparation of 1-methyl-1-((erucylamido-) ethyl)-2-erucyl immidazoliniummethyl sulfate.

3132 g (4.62 moles) of erucic acid and 216 g (2.1 moles) ofdiethylenetriamine are placed in a dry stirred pressure vessel fittedwith a nitrogen inlet. The vessel is purged with nitrogen and heated to170° C. for 4-5 hours. The reaction mixture is then heated to 180° C.and vacuum is applied for another 4-5 hours. The reaction mixture iscooled to 95-100° C. and approximately 1.5 kg of cetearyl alcohol isadded. The reaction mixture is further cooled to 75-80° C. and 250 g ofdimethyl sulfate is slowly added with stirring. Once all dimethylsulfate is added, the reaction mixture is held at 75-80° C. forapproximately one hour, providing 1-methyl-1-((erucylamido-)ethyl)-2-erucyl immidazolinium methyl sulfate as the product.

EXAMPLE 2

Preparation of 1-methyl-1-(erucic rapeseed-)-ethyl)-2-(erucic rapeseed-)immidazolinium methyl sulfate (mixture of dialkyl immidazoline quats ofhydrogenated rapeseed oil).

1843.6 g (1.88 moles) of hydrogenated rapeseed oil and 283.34 g (2.75moles) of diethylenetriamine were placed in a dry stirred pressurevessel fitted with a nitrogen inlet. The vessel was purged with nitrogenand heated to 165° C. for 5 hours until a base value of 76 was reached.The reaction mixture was then heated to 190° C. and vacuum was appliedfor 5 hours to obtain a 94% tertiary amine content. The resultingimmidazoline intermediate was then cooled to 95° C. and 1772 g ofcetearyl alcohol were added to act as solvent. The reaction mixture wasfurther cooled to 85° C. and 330 g (2.6 moles) of dimethyl sulfate wereslowly added over a 30 minute period with stirring. Once all dimethylsulfate was added, the reaction mixture was held at 85-90° C. foranother 60 minutes. The resulting light yellow solid product includeddi-hydrogenated rapeseed oil imidazoline quat and cetearyl alcohol. Thecationic activity of the mixture was 54%. The product was capable ofbeing flaked or pastillated.

EXAMPLE 3

Preparation of 1-methyl-1-N-(n-propyl)-2-erucyl immidazolinium methylsulfate.

% of total Total cationic cationic Component Ingredient activityactivity Component Mixture of Table 1 70% 45% (a) Component Compound(XXIII) 30% (b) Solvent Mixture of cetearyl alcohol (80%) and —1,3-butanediol (20%)

EXAMPLE 5

Quat Raw Material 2

Quat Raw Material 2 has the following composition:

% of total Total cationic cationic Component Ingredient activityactivity Component di-behenyl 60% 25% (a) immidazolinium methasulfateComponent Cetrimonium 40% (b) methosylfate Solvent Cetyl alcohol —

EXAMPLE 6

Quat Raw Material 3

Quat Raw Material 2 has the following composition:

% of total Total cationic cationic Component Ingredient activityactivity Component di-behenyl 70% 25% (a) immidazolinium methasulfateComponent Cetrimonium  3% (b) methosylfate Solvent Cetyl alcohol —

EXAMPLE 7

Quat Raw Material 4

Quat Raw Material 2 has the following composition:

% of total Total cationic cationic Component Ingredient activityactivity Component Mixture of Table 1 60% 25% (a) Component Lauryltrimethyl 40% (b) ammonium chloride Solvent Cetyl alcohol —

EXAMPLE 8

Sunscreen Lotion

A sunscreen lotion includes the following ingredients:

Ingredient(s) % W/W Phase A Di-erucic 1.0 imidazoline quatBehentrimonuim 1.0 Chloride Benzophenone 3 5.0 Cetearyl Alcohol 4.0Crodamol OS (Octyl 15.0 Stearate) Octyl 7.5 Methoxycinnamate Phase BWater 65.50 Phase C Germaben II 1.0 (preservative)

The ingredients of Phase A are combined and heated to 75° C. In aseparate vessel, the ingredients of Phase B are also combined and heatedto 75° C. Phase A is added to Phase B with stirring, and the stirring iscontinued while the combined phases are cooled to 40° C. Phase C. isadded, the cooling is continued to 25° C, providing the desired lotion.

EXAMPLE 9

Sunscreen Spray Lotion

A sunscreen spray lotion includes the following ingredients:

Ingredient % W/W Phase A Di-erucic 1.0 imidazoline quat Cetrimonium 1.0Chloride PPG-3 Benzyl 10.0 Myristate Benzophenone 3 6.0 Octyl 7.0Methoxycinnamate Menthyl 5.0 Anthranilate Cromollient SCE 3.0 (Di-PPG-2Myreth-10 Adipate) Phase B Water 66 Sodium Hydroxide 0.1 Phase CGermaben II 1.0 (preservative)

The ingredients of Phase A are combined and heated to 75° C. In aseparate vessel, the ingredients of Phase B are also combined and heatedto 75° C. Phase A is added to Phase B with stirring, and the stirring iscontinued while the combined phases are cooled to 40° C. Phase C. isadded, the cooling is continued to 25° C, providing the desired lotion.

EXAMPLE 11

Hair Conditioner

Ingredient % W/W Phase A Di-C20-24 1.0 Imidazoline Quat Cetrimonium 1.0Chloride Cromollient SCE 4.0 (Di-PPG-2 Myreth- 10 Adipate) Cetyl Alcohol4.0 Phase B Water 89 Phase C Germaben II 1.0 (preservative)

The ingredients of Phase A are combined and heated to 75° C. In aseparate vessel, the ingredients of Phase B are also combined and heatedto 75° C. Phase A is added to Phase B with stirring, and the stirring iscontinued while the combined phases are cooled to 40° C. Phase C. isadded, the cooling is continued to 25° C., providing the desired lotion.

EXAMPLE 12

Conditioning Shampoo

A hair conditioner includes the following ingredients:

Ingredient % W/W Phase A Ammonium Lauryl 25.0 Sulfate Ammonium Laureth12.0 Sulfate Crosultaine C-50 3.0 (Cocamidopropyl Hydroxysultaine)Lauramide DEA 1.0 Cromollient SCE 4.0 (Di-PPG-2 Myreth-10 Adipate)Germaben II 1.0 (Preservative) Phase B Di-Erucic 2.0 Imidazoline Quat

The ingredients of phase A are combined and heated to 60° C. Phase B isadded to the combined phase A and with continued stirring while allowingthe mixture to cool to 25° C.

EXAMPLE 13

Soft & Shine Conditioner

A soft and shine conditioner includes the following ingredients.

Ingredient % W/W Phase A Water 86.26 Mixture of Di-behenyl 2.14imidazolinium Methosulfate and Cetrimonium Methasulfate (7/3 w/w) inCetearyl alcohol (70% actives) CRODACOL C-70 (Cetyl Alcohol) 1.00CRODACOL S-70 (Stearyl Alcohol) 3.00 CRILLET 3 (Polysorbate 60) 1.00Part B INCROMINE SB (Stearamidopropyl 0.5 Dimethylamine)Cyclopentasiloxane (and) 4.0 Dimethicone (1) Dimethicone (2) 0.5Disodium EDTA 0.2 Propylene Glycol (and) 1.00 Diazolidinyl Urea (and)Methylparaben (and) Propylparaben (3) Citric acid 0.4 Part C Germaben II1.0 (Preservative)

EXAMPLE 14

Vitamin E-Containing Conditioner

The vitamin E-containing conditioner has the following ingredients.

Ingredient % W/W Phase A Deionized Water 92.50 CRODACOL S-70 3.80(Stearyl Alcohol) Mixture of Di-behenyl 2.20 imidazolinium Methosulfateand Cetrimonium Methasulfate (7/3 w/w) in Cetearyl alcohol (70% actives)Part B DL-α Tocopherol 0.50 Acetate (1) Part C Propylene Glycol 1.00(and) Diazolidinyl Urea (and) Methylparaben (and) Propylparaben (2)Deposition of Vitamin E (mg of Vit E/100 g of hair) Ingredient VirginHair Bleached Hair Behentrimonium Chloride 86.3 57.6 Mixture ofDi-behenyl 180 80.9 imidazolinium Methosulfate and CetrimoniumMethasulfate (7/3 w/w)

EXAMPLE 16

Deposition of Vitamin E (Comparative Experiment 2).

Test conditioning shampoo formulations A and B were prepared using amixture of Di-behenyl imidazolinium Methosulfate and CetrimoniumMethasulfate in 7/3 w/w ratio of quats to one another as the activeconditioning ingredient. The added conditioning ingredient, which isgenerally derived from HEAR oil, contained 70% active quats by cationicactivity in cetearyl alcohol. Test formulation A contained 1% of quat bycationic activity and test formulation A contained 0.5% of quat bycationic activity. Polyquaternium-10, a well-known polymericconditioner, was used in the reference formulation C. The smaller amountof Polyquaternium-10 was used to reflect the cost benefit consideration.

Hair samples were treated with the respective conditioning shampoo for 3minutes and rinsed off under 40° C. running tap water with a flow rateof 2.51/min for 20 seconds. The total substantivity was determined bytwo consecutive extractions by PVCS Method # 7-1. Only trace of VitaminE was detected in the third extraction solution.

The determined total substantivity of Vitamin E delivered from theseconditioning shampoo samples is presented below:

Average Substantivity (mg Vit E/100 g hair) by PVCS Method # 7-1Ingredient//Amount added First Second to the Test Shampoo extractionextraction Total Mixture of Di-behenyl 52.7 23.1 75.8 imidazoliniumMethosulfate and Cetrimonium Methasulfate (7/3 w/w)// 1% cationicactivity Mixture of di-behenyl 46.4 44.6 91.0 imidazolinium methosulfateand cetrimonium methasulfate (7/3 w/w ratio) in cetearyl alcohol (70%actives)// 0.5% cationic activity Polyquaternium-10// 24.3 15.6 39.90.3% by cationic activity

The conditioning shampoo samples containing di-behenyl imidazoliniummethosulfate showed better deposition of Vitamin E onto hair surfacethan the sample containing Polyquaternium-10. Also, the deposition ofVitamin E on hair surface was enhanced by an increase in theconcentration of di-behenyl imidazolinium methosulfate in theformulation.

EXAMPLE 17

Emulfication/Performance Comparison: Stability.

Cetrimonium Methosulfate, Diphenyl Imidazolinium Methosulfate, and amixture of Diphenyl Imidazolinium Methosulfate +Cetrimonium Methosulfate+Cetearyl alcohol were used to evaluate emulsification vs. performanceof quat mixtures.

Lotions were prepared as shown below:

Ingredient AP-1 (%) AP-2 (%) AP-3 (%) Cetrimonium quat 1.5 0 0 Dibehenyl0 1.5 0 Imidazolinium quat 40:60 mix of 0 0 1.5 Cetrimonium:DibehenylImidazolinium Crodacol S-70 4.5 4.5 4.5 Deionized Water 94 94 94

Stability of each lotion at 24 hours was evaluated. Lotion AP-1(Cetrimonium Methosulfate alone) was stable. Lotion AP-2 (DiphenylImidazolinium alone) was unstable. Lotion AP-3 (60:40 mixture ofCetrimonium Methosulfate and Diphenyl Imidazolinium) was stable.

EXAMPLE 18

Emulfication/Performance Comparison (Performance).

Only stable lotions were evaluated for performance.

Evaluation procedure was as follows. Virgin (V) and Bleached (B) hairtresses weighing about 3-4 g each were washed with a standard shampoobase and allowed to dry overnight. The tresses where then treated withLotions AP-1 and AP-3 and allowed to dry in a constant temperature andhumidity chamber at 25° C. and 50% relative humidity. Combing force wasmeasured using a Dia-Stron Miniature Tensile Tester. Total Work measuresthe force necessary to pass a comb through a hair tress and basically isa measurement of the Overall Combing properties of the hair. Peak Loadis the highest force seen during combing and is indicative of how well aproduct detangles hair during combing.

The results were as follows:

AP-1 (%) AP-3 (%) Peak Load (B) 54.4 70.7 Total load (B) 25.5 38.1 PeakLoad (V) 46.3 58.7 Total load (V) 15.5 20.7

The data show that combinations of Diphenyl Imidazolinium Methosulfateand Cetrimonium Methosulfate produce stable lotions that have improvedhair-conditioning properties over just Cetrimonium Methosulfate lotions.

The results show that Lotion AP-3 was better at reducing Peak Loadforces and Total Work on both bleached and virgin hair compared toLotion AP-1.

Unless stated to the contrary, any use of the words such as “including,”“containing,” “comprising,” “having” and the like, means “includingwithout limitation” and shall not be construed to limit any generalstatement that it follows to the specific or similar items or mattersimmediately following it.

Although the invention herein has been described with reference toparticular embodiments, it is to be understood that these embodimentsare merely illustrative of the principles and applications of thepresent invention. It is therefore to be understood that numerousmodifications may be made to the illustrative embodiments and that otherarrangements may be devised without departing from the spirit and scopeof the present invention as defined by the appended claims.

1. A composition comprising: (a) a mixture of dialkyl imidazoline quatsin an amount of from about 10% to about 90% by weight of thecomposition; and (b) at least one monoalkyl quat in an amount of fromabout 10% to about 90% by weight of the composition.
 2. The compositionof claim 1, wherein said mixture of dialkyl imidazoline quats arepresent in an amount of from about 20% to about 80% and said at leastone monoalkyl quat is present in an amount of from about 20% to about80% by weight of the composition.
 3. The composition of claim 2, whereinsaid mixture of dialkyl imidazoline quats are present in an amount offrom about 40% to about 70% and said at least one monoalkyl quat ispresent in an amount of from about 30% to about 60% by weight of thecomposition.
 4. The composition of claim 1, wherein at least a portionof said mixture includes at least one dialkyl imidazolineimidazolinequat having at least one C₂₀-C₂₄ alkyl group; the C₂₀₋₂₄ substitutioncontent of said mixture being from about 10% to about 95% with respectto C₁₀₊ reference substitution range.
 5. The composition of claim 1,wherein said at least one monoalkyl quat is a monoalkyl imidazoline quator mixture of monoalkyl imidazoline quats.
 6. The composition of claim1, wherein said at least one monoalkyl quat is a monoalkyl ammoniumquat.
 7. The composition of claim 1, wherein said dialkyl imidazolinequats include those derived from HEAR oil and said monoalkyl quat is aquat including cetyl ammonium chloride, cetyl ammonium bromide, laurylammonium chloride, lauryl ammonium bromide, stearyl ammonium chloride,stearyl ammonium bromide, cetyl dimethyl ammonium chloride, cetyldimethyl ammonium bromide, lauryl dimethyl ammonium chloride, lauryldimethyl ammonium bromide, stearyl dimethyl ammonium chloride, stearyldimethyl ammonium bromide, cetyl trimethyl ammonium chloride, cetyltrimethyl ammonium bromide, lauryl trimethyl ammonium chloride, lauryltrimethyl ammonium bromide, stearyl trimethyl ammonium chloride, stearyltrimethyl ammonium bromide, lauryl dimethyl ammonium chloride,stearamidopropyl PG-dimonium chloride phosphate, stearamidopropylethyldimonium ethosulfate, stearamidopropyl dimethyl (myristyl acetate)ammonium chloride, stearamidopropyl dimethyl cetearyl ammonium tosylate,stearamidopropyl dimethyl ammoniun chloride, stearamidopropyl anddimethyl ammonium lactate, or mixtures thereof.
 8. The composition ofclaim 1, wherein said mixture of dialkyl imidazoline guats includes atleast one dialkyl imidazoline quat having at least one alkyl grouphaving from 16 to 30 carbon atoms.
 9. The composition of claim 8,wherein said at least one dialkyl imidazoline quat includes at least onealkyl group having from 20 to 30 carbon atoms.
 10. The composition ofclaim 9, wherein said at least one dialkyl imidazoline quat includes atleast one alkyl group having from 20 to 24 carbon atoms.
 11. Thecomposition of claim 1, wherein said at least one monoalkyl quatincludes at least one alkyl group having from 16 to 30 carbon atoms. 12.The composition of claim 11, wherein said at least one monoalkyl quatincludes at least one alkyl group having from 20 to 30 carbon atoms. 13.The composition of claim 12, wherein said at least one monoalkyl guatincludes at least one alkyl group having from 20 to 24 carbon atoms. 14.The composition of claim 1, wherein said mixture of dialkyl imidazolinequats is present in the amount of from about 60% to about 80% by weightof the composition, and said at least one monoalkyl guat is a monoalkylammonium quat present in the amount of from about 20% to about 40% byweight of the composition.
 15. The composition of claim 14, wherein saidmixture of dialkyl imidazoline quats includes at least one dialkylimidazoline quat with at least one alkyl group having from 20 to 24carbon atoms and said monoalkyl ammonium quat includes at least onealkyl group having from 16 to 24 carbon atoms.
 16. The composition ofclaim 1, wherein said mixture of dialkyl imidazoline quats includes atleast one dialkyl imidazoline quat of the formula (I):

where X is a salt-forming anion selected from the group consisting ofchloride, bromide, iodide, fluoride, sulfate, methyl sulfate,methanebenzylsulfonate, phosphate, nitrite, nitrate, carboxylate, andmixtures thereof; a is the ionic charge of X; R¹, R², and R³ areindependently hydrogen, C₁-C₃₀ alkyl, C₁-C₃₀ alkylhydroxy, C₁-C₃₀ alkylamido R_((C1-C6)), C₁-C₃₀ alkylaryl amido R_((C1-C6)) or C₁-C₃₀alkylhydroxy amido R_((C1-C6)), R_((C1-C6)) being C₁-C₆ alkylene orbenzyl; two of R¹, R², and R³ are independently C₁₀-C₃₀ alkyl, C₁₀-C₃₀alkylhydroxy, C₁₀-C₃₀ alkyl amido R_((C1-C6)), C₁₀-C₃₀ alkylaryl amidoR_((C1-C6)) or C₁₀-C₃₀ alkylhydroxy amido R_((C1-C6)); the remaining oneof R¹, R² and R³ is hydrogen, C₁-C₈ alkyl, C₁-C₈ alkylhydroxy, C₁-C₈alkyl amido R_((C1-C6)), C₁-C₈ alkylaryl amido R_((C1-C6)) or C₁-C₈alkylhydroxy amido R_((C1-C6)); R⁴, R⁵, R⁶, and R⁷, same or different,are independently hydrogen, alkyl, arylalkyl, alkylaryl, fluoro, bromo,chloro, iodo, acetoxy, alkylacetoxy, arylacetoxy, carboxy, alkylcarboxy,hydroxy or alkoxyhydroxy.
 17. The composition of claim 16, wherein R¹ isC₁₀-C₃₀ alkyl or C₁₀-C₃₀ alkylhydroxy, R² is C₁-C₆ alkyl, R³ is C₁₀-C₃₀alkyl amido R_((C1-C6)) or C₁₀-C₃₀ alkylhydroxy amido R_((C1-C6)), andR⁴, R⁵, R⁶, and R⁷ are independently hydrogen or C₁-C₈ alkyl.
 18. Thecomposition of claim 17, wherein R¹ is C₁₀-C₃₀ alkyl, R² is methyl, R³is C₁₀-C₃₀ alkylhydroxy amido C₁-C₃ alkylene, R⁴, R⁵, R⁶, and R⁷ arehydrogen, and X is chloride or methyl sulfate.
 19. The composition ofclaim 17, wherein R¹ is C₁₀-C₃₀ alkyl, R² is methyl, R³ is C₁₀-C₃₀ alkylamido C₁-C₃ alkylene, R⁴, R⁵, R⁶, and R⁷ are hydrogen, and X is chlorideor methyl sulfate.
 20. The composition of claim 19, wherein R³ isC₁₀-C₃₀ alkyl amido ethylene.
 21. The composition of claim 1, whereinsaid mixture of dialkyl imidazoline quats includes at least one dialkylimidazoline quat of the formula (II):

wherein X is a salt-forming anion selected from the group consisting ofchloride, bromidi, iodide, fluoride, sulfate, methyl sulfate,methanebenzylsulfonate, phosphate, nitrite, nitrate, carboxylate, andmixtures thereof; a is the ionic charge of X; n varies from 1 to 3; m is1 or 2; R⁸ and R¹¹, same or different, are independently C₁₆-C₃₀ alkylor C₁₆-C₃₀ alkylhydroxy; R⁹ is hydrogen or C₁-C₃ alkyl; and R¹⁰ ishydrogen, alkyl, arylalkyl, alkylaryl, fluoro, bromo, chloro, iodo,acetoxy, alkylacetoxy, arylacetoxy, carboxy, alkylcarboxy, hydroxy oralkoxyhydroxy.
 22. The composition of claim 21, wherein R⁹ is C₁-C₃alkyl, R¹⁰ is hydrogen, n is 2, and m is
 2. 23. The composition of claim22, wherein R⁸ is C₁₆-C₃₀ alkyl or C₁₆-C₃₀ alkylhydroxy and R¹¹ isC₁₆-C₃₀ alkyl or C₁₆-C₃₀ alkylhydroxy.
 24. The composition as in any ofclaims 1 and 21, wherein said at least one said monoalkyl quat has thestructure

wherein Y is a salt-forming anion selected from the group consisting ofchloride, bromide, iodide, fluoride, sulfate, methyl sulfate,methanebenzylsulfonate, phosphate, nitrite, nitrate, carboxylate, andmixtures thereof; b is the ionic charge of Y; Q₁ is selected from thegroup consisting of C₁₂-C₂₂ alkyl, C₁₂-C₂₂ alkyl amido C₁-C₆ alkylene,and C₁₂-C₂₂ alkylhydroxy; and Q₂, Q₃ and Q₄ are independently C₁-C₆alkyl or benzyl.
 25. The composition of claim 1, wherein said monoalkylquat is a monoalkyl ammonium quadt selected from the group consisting ofcetyl, lauryl, and stearyl.
 26. The composition of claim 23, whereinboth R⁸ and R¹¹ are behenyl radicals of the structure —C₂₁H₄₃.
 27. Thecomposition of claim 23, wherein both R⁸ and R¹¹ are derived from alkylgroups present in a hydrogenated HEAR oil and X is methyl sulfate. 28.The composition of claim 27, wherein said at least one monoalkyl quat iscetrimonium methosulfate.
 29. The composition of claim 28, wherein saidmixture of dialkyl imidazoline quats and said cetrimonium methosulfateare present in the ratio of approximately 7 to 3 by weight.
 30. Thecomposition as in any of claims 1 and 21, wherein said at least onemonoalkyl quat is a monoalkyl imidazoline quat of the formula (IV):

wherein X is a salt-forming anion selected from the group consisting ofchloride, bromide, iodide, fluoride, sulfate, mathyl sulfate,methanebenzylsulfonate, phosphate, nitrite, nitrate, carboxylate, andmixtures thereof; a is the ionic charge of X; R¹⁵, R¹⁶ and R¹⁷ areindependently hydrogen, C₁-C₃₀ alkyl, C₁-C₃₀ alkylhydroxy, C₁-C₃₀ alkylamido R_((C1-C6)), C₁-C₃₀ alkylaryl amido R_((C1-C6)), or C₁-C₃₀alkylhydroxy amido R_((C1-C6)), wherein R_((C1-C6)) is a C₁-C₆ alkyleneor benzyl; one of R¹⁵, R¹⁶ and R¹⁷ is C₁-C₃₀ alkyl, C₁₀-C₃₀alkylhydroxy, C₁₀-C₃₀ alkyl amido R_((C1-C6)), C₁₀-C₃₀ alkylaryl amidoR_((C1-C6)) or C₁₀-C₃₀ alkylhydroxy amido R_((C1-C6)); the remaining twoof R¹⁵, R¹⁶ and R¹⁷ are independently hydrogen, C₁-C₈ alkyl, C₁-C₈alkylhydroxy, C₁-C₈ alkyl amido R_((C1-C6)), C₁-C₈ alkylaryl amidoR_((C1-C6)), or C₁-C₈ alkylhydroxy amido R_((C1-C6)); R¹⁸, R¹⁹, R²⁰, andR²¹, same or different, are independently selected from the groupconsisting of hydrogen, alkyl, arylalkyl, alkylaryl, fluoro, iodo, bromoand chloro, acetoxy, alkylacetoxy, arylacetoxy, carboxy, alkylcarboxy,hydroxy, and alkoxyhydroxy.
 31. The composition of claim 30, whereinR¹⁸, R¹⁹, R²⁰, and R²¹ are independently hydrogen or C₁-C₈ alkyl. 32.The composition as in any one of claims 1, 7, 14, 21, and 29, furthercomprising at least one hydrophobic ingredient.
 33. The composition ofclaim 32, wherein said at least one hydrophobic ingredient is selectedfrom the group consisting of botanical extracts, vitamin E, vitamin A,silicones, waxes and antioxidants.
 34. The composition of claim 32,wherein said at least one hydrophobic ingredient is vitamin E.
 35. Thecomposition as in any one of claims 1, 7, 14, 21, and 29, furthercomprising one or more preservatives, fragrances, foam boosters,conditioners and emollients.
 36. The composition as in any one of claims1, 7, 14, 21, and 29, further comprising at least one active ingredientpresent in the amount of between about 0.20 and about 40.0 percent byweight of the composition.
 37. The composition of claim 36, wherein saidactive ingredient is selected from the group consisting of a sunscreen,pigment, moisturizer, film former, detergent, thickening agent,emulsifier, antiseptic agent, conditioner and deodorant.
 38. Thecomposition as in any one of claims 1, 7, 14, 21, and 29, furthercomprising at least one surfactant present in the amount of from about1% to about 75% by weight of the composition.
 39. The method of claim38, wherein said surfactant is selected from the group consisting ofnon-ionic surfactants, anionic surfactants, cationic, surfactants andamphoteric surfactants.
 40. The composition as in any one of claims 1,7, 14, 21, and 29, which is a raw material quat.
 41. The composition ofclaim 40, further comprising a carrier.
 42. The composition of claim 41having a cationic activity of greater than 20%.
 43. The composition ofclaim 42, wherein said cationic activity is greater than 35%.
 44. Thecomposition of claim 43, wherein said cationic activity is greater than50%.
 45. The composition as in any one of claims 1, 7, 14, 21, and 29,which is a cosmetic or personal care product selected from the groupconsisting of shampoo, hair conditioner, sunscreen formulation, babyshampoo, baby bath product, hand dishwashing liquid, body wash, facialwash, non-woven toilette, baby wipe and bubble bath product.
 46. Thecomposition of claim 45, wherein said cosmetic or personal care productis a non-aqueous topical formulation.
 47. The composition of claim 45,wherein said cosmetic or personal care product is an aqueous topicalformulation.
 48. The composition of claim 4, wherein the at least oneC₂₀-C₂₄ alkyl group is a C₁₈ alkyl group.
 49. A composition comprising:(a) at least one dialkyl quat in the amount of from about 10% to about90% by weight of the composition; and (b) a mixture of monoalkylimidazoline quat in the amount of from about 10% to about 90% by weightof the composition.
 50. The composition of claim 49, wherein said atleast one dialkyl quat is present in an amount of from about 20% toabout 80% and said mixture of monoalkyl imidazoline quats is present inan amount of from about 20% to about 80% by weight of the composition.51. The composition of claim 50, wherein said at least one dialkyl quatis present in an amount of from about 40% to about 70% and said mixtureof monoalkyl imidazoline quats is present in an amount of from about 30%to about 60% by weight of the composition.
 52. The composition of claim49, wherein said at least one dialkyl quat is a dialkyl imidazoline quator mixture of dialkyl imidazoline quats.
 53. The composition of claim49, wherein said at least one dialkyl quat includes at least one alkylgroup having from 16 to 30 carbon atoms.
 54. The composition of claim53, wherein said at least one dialkyl quat includes at least one alkylgroup having from 20 to 30 carbon atoms.
 55. The composition of claim54, wherein said at least one dialkyl quat includes at least one alkylgroup having from 20 to 24 carbon atoms.
 56. The composition of claim49, wherein said mixture of monoalkyl imidazoline quat includes at leastone monoalkyl imidazoline quat having at least one alkyl group of 16 to30 carbon atoms.
 57. The composition of claim 56, wherein said mixtureof monoalkyl imidazoline quat includes at least one monoalkylimidazoline quat having at least one alkyl group of 20 to 30 carbonatoms.
 58. The composition of claim 57, wherein said mixture ofmonoalkyl imidazoline quat includes at least one monoalkyl imidazolinequats having at least one alkyl group of 20 to 24 carbon atoms.
 59. Thecomposition of claim 49, wherein said dialkyl quat is a dialkylimidazoline quat of the formula (I):

where X is a salt-forming anion selected from the group consisting ofchloride, bromide, iodide, fluoride, sulfate, methyl sulfate,methanebenzylsulfonate, phosphate, nitrite, nitrate, carboxylate, andmixtures thereof; a is the ionic charge of X; R¹, R², and R³ areindependently hydrogen, C₁-C₃₀ alkyl, C₁-C₃₀ alkylhydroxy, C₁-C₃₀ alkylamido R_((C1-C6)), C₁-C₃₀ alkylaryl amido R_((C1-C6)) or C₁-C₃₀alkylhydroxy amido R_((C1-C6)), R_((C1-C6)) being C₁-C₆ alkylene orbenzyl; two of R¹, R², and R³ are independently C₁₀-C₃₀ alkyl, C₁₀-C₃₀alkylhydroxy, C₁₀-C₃₀ alkyl amido R_((C1-C6)), C₁₀-C₃₀ alkylaryl amidoR_((C1-C6)) or C₁₀-C₃₀ alkylhydroxy amido R_((C1-C6)); the remaining oneof R¹, R² and R³ is hydrogen, C₁-C₈ alkyl, C₁-C₈ alkylhydroxy, C₁-C₈alkyl amido R_((C1-C6)), C₁-C₈ alkylaryl amido R_((C1-) _(C6)) or C₁-C₈alkylhydroxy amido R_((C1-C6)); R⁴, R⁵, R⁶, and R⁷, same or different,are independently hydrogen, alkyl, arylalkyl, alkylaryl, fluoro, bromo,chloro, iodo, acetoxy, alkylacetoxy, arylacetoxy, carboxy, alkylcarboxy,hydroxy or alkoxyhydroxy.
 60. The composition of claim 59, wherein R¹ isC₁₀-C₃₀ alkyl or C₁₀-C₃₀ alkylhydroxy, R² is C₁-C₆ alkyl, R³ is C₁₀-C₃₀alkyl amido R_((C1-C6)) or C₁₀-C₃₀ alkylhydroxy amido R_((C1-C6)), andR⁴, R⁵, R⁶, and R⁷ are independently hydrogen or C₁-C₈ alkyl.
 61. Thecomposition of claim 60, wherein R¹ is C₁₀-C₃₀ alkyl, R² is methyl, R³is C₁₀-C₃₀ alkylhydroxy amido C₁-C₃ alkylene, R⁴, R⁵, R⁶, and R⁷ arehydrogen, and X is chloride or methyl sulfate.
 62. The composition ofclaim 60, wherein R¹ is C₁₀-C₃₀ alkyl, R² is methyl, R³ is C₁₀-C₃₀ alkylamido C₁-C₃ alkylene, R⁴, R⁵, R⁵, and R⁷ are hydrogen, and X is chlorideor methyl sulfate.
 63. The composition of claim 62, wherein R³ isC₁₀-C₃₀ alkyl amido ethylene.
 64. The composition of claim 49, whereinsaid at least one dialkyl quat is a dialkyl imidazoline quat of theformula (II):

wherein X is a salt-forming anion selected from the group consisting ofchloride, bromide, iodide, fluoride, sulfate, methyl sulfate,methanebenzylsulfonate, phosphate, nitrite, nitrate, carboxylate, andmixtures thereof; a is the ionic charge of X; n varies from 1 to 3; m is1 or 2; R⁸ and R¹¹, same or different, are independently C₁₆-C₃₀ alkylor C₁₆-C₃₀ alkylhydroxy; R⁹ is hydrogen or C₁-C₃ alkyl; and R¹⁰ ishydrogen, alkyl, arylalkyl, alkylaryl, fluoro, bromo, chloro, iodo,acetoxy, alkylacetoxy, arylacetoxy, carboxy, alkylcarboxy, hydroxy oralkaxyhydroxy.
 65. The composition of claim 64, wherein R⁹ is C₁-C₃alkyl, R¹⁰ is hydrogen, n is 2, and m is
 2. 66. The composition of claim65, wherein R⁸ is C₁₆-C₃₀ alkyl or C₁₆-C₃₀ alkylhydroxy and R¹¹ isC₁₆-C₃₀ alkyl or C₁₆-C₃₀ alkylhydroxy.
 67. The composition of claim 66,wherein both R⁸ and R¹¹ are behenyl radicals of the structure C₂₁H₄₃.68. The composition of claim 66, wherein both R⁸ and R¹¹ are derivedfrom alkyl groups present in a hydrogenated HEAR oil and X is methylsulfate.
 69. The composition as in any one of claims 59 and 64, whereinsaid mixture of monoalkyl imidazoline quats includes a monoalkylimidazoline quats of the formula (IV):

wherein X is a salt-forming anion selected from the group consisting ofchloride, bromide, iodide, fluoride, sulfate, methyl sulfate,methanebenzylsulfonate, phosphate, nitrite, nitrate, carboxylate, andmixtures thereof; a is the ionic charge of X; R¹⁵, R¹⁶ and R¹⁷ areindependently hydrogen, C₁-C₃₀ alkyl, C₁-C₃₀ alkylhydroxy, C₁-C₃₀ alkylamido R_((C1-C6)), C₁-C₃₀ alkylaryl amido R_((C1-C6)), or C₁-C₃₀alkylhydroxy amido R^((C1-C6)), wherein R_((C1-C6)) is a C₁-C₆ alkyleneor benzyl; one of R¹⁵, R¹⁶ and R¹⁷ is C₁-C₃₀ alkyl, C₁₀-C₃₀alkylhydroxy, C₁₀-C₃₀ alkyl amido R_((C1-C6)), C₁₀-C₃₀ alkylaryl amidoR_((C1-C6)) or C₁₀-C₃₀ alkylhydroxy amido R_((C1-C6)); the remaining twoof R¹⁵, R¹⁶ and R¹⁷ are independently hydrogen, C₁-C₈ alkyl, C₁-C₈alkylhydroxy, C₁-C₈ alkyl amido R_((C1-C6)), C₁-C₈ alkylaryl amidoR_((C1-C6)), or C₁-C₈ alkylhydroxy amido R_((C1-C6)); R¹⁸, R¹⁹, R²⁰, andR²¹, same or different, are independently selected from the groupconsisting of hydrogen, alkyl, arylalkyl, alkylaryl, fluoro, iodo, bromoand chloro, acetoxy, alkylacetoxy, arylacetoxy, carboxy, alkylcarboxy,hydroxy, and alkoxyhydroxy.
 70. The composition of claim 69, whereinR¹⁸, R¹⁹, R²⁰, and R²¹ are independently hydrogen or C₁-C₈ alkyl. 71.The composition of claim 1 wherein said mixture of dialkyl imidazolinequats include dialkyl quats which are not imidazoline quats.
 72. Thecomposition of claim 49 wherein said mixture of monoalkyl imidazolinequats include monoalkyl quats which are not imidazoline quats.
 73. Thecomposition of any one of claims 49 and 64, wherein said mixture ofmonoalkyl imidazoline quats has the structure

wherein Y is a salt-forming anion selected from the group consisting ofchloride, bromide, iodide, fluoride, sulfate, methyl sulfate,methanebenzylsulfonate, phosphate, nitrite, nitrate, carboxylate, andmixtures thereof; b is the ionic charge of Y; Q₁ is selected from thegroup consisting of C₁₂-C₂₂ alkyl, C₁₂-C₂₂ alkyl amido C₁-C₆ alkylene,and C₁₂-C₂₂ alkylhydroxy; and Q₂, Q₃ and Q₄ are independently C₁-C₆alkyl or benzyl.
 74. The composition of claim 73, wherein said monoalkylquat is a monoalkyl ammonium quat selected from the group consisting ofcetyl, lauryl, and stearyl.
 75. The composition of claim 49, whereinsaid monoalkyl imidazoline quat is a cetrimonium quat.
 76. Thecomposition of claim 49, wherein said dialkyl quat include a mixture ofdialkyl imidazoline quats derived from HEAR oil or hydrogenated HEARoil.
 77. The composition of claim 49, wherein said mixture of monoalkylimidazoline quats includes a monoalkyl imidazoline quats of the formula(IV):

wherein X is a salt-forming anion selected from the group consisting ofchloride, bromide, iodide, fluoride, sulfate, methyl sulfate,methanebenzylsulfonate, phosphate, nitrite, nitrate, carboxylate, andmixtures thereof; a is the ionic charge of X; R¹⁵, R¹⁶ and R¹⁷ areindependently hydrogen, C₁-C₃₀ alkyl, C₁-C₃₀ alkylhydroxy, C₁-₃₀ alkylamido R_((C1-C6)), C₁-C₃₀ alkylaryl amido R_((C1-C6)), or C₁-C₃₀alkylhydroxy amido R_((C1-C6)), wherein R_((C1-C6)) is a C₁-C₆ alkyleneor benzyl; one of R¹⁵, R¹⁶ and R¹⁷ is C₁-C₃₀ alkyl, C₁₀-C₃₀alkylhydroxy, C₁₀-C₃₀ alkyl amido R_((C1-C6)), C₁₀-C₃₀ alkylaryl amidoR_((C1-C6)) or C₁₀-C₃₀ alkylhydroxy amido R_((C1-C6)); the remaining twoof R¹⁵, R¹⁶ and R¹⁷ are independently hydrogen, C₁-C₈ alkyl, C₁-C₈alkylhydroxy, C₁-C₈ alkyl amido R_((C1-C6)), C₁-C₈ alkylaryl amidoR_((C1-C6)), or C₁-C₈ alkylhydroxy amido R_((C1-C6)); R¹⁸, R¹⁹, R²⁰, andR²¹, same or different, are independently selected from the groupconsisting of hydrogen, alkyl, arylalkyl, alkylaryl, fluoro, iodo, bromoand chloro, acetoxy, alkylacetoxy, arylacetoxy, carboxy, alkylcarboxy,hydroxy, and alkoxyhydroxy.
 78. The composition as in any one of claims49, 59, 64 and 77 further comprising at least one hydrophobicingredient.
 79. The composition of claim 78, wherein said at least onehydrophobic ingredient is selected from the group consisting ofbotanical extracts, vitamin E, vitamin A, silicones, waxes andantioxidants.
 80. The composition of claim 78, wherein said at least onehydrophobic ingredient is vitamin E.
 81. The composition as in any oneof claims 49, 59, 64 and 77 further comprising one or morepreservatives, fragrances, foam boosters, conditioners and emollients.82. The composition as in any one of claims 49, 59, 64 and 77 furthercomprising at least one active ingredient present in the amount ofbetween about 0.20 and about 40.0 percent by weight of the composition.83. The composition of claim 80, wherein said active ingredient isselected from the group consisting of a sunscreen, pigment, moisturizer,film former, detergent, thickening agent, emulsifier, antiseptic agent,conditioner and deodorant.
 84. The composition as in any one of claims49, 59, 64 and 77 further comprising at least one surfactant present inthe amount of from about 1% to about 75% by weight of the composition.85. The method of claim 84, wherein said surfactant is selected from thegroup consisting of non-ionic surfactants, anionic surfactants, cationicsurfactants and amphoteric surfactants.
 86. The composition as in anyone of claims 49, 59, 64 and 77, which is a raw material quat.
 87. Thecomposition of claim 86, further comprising a carrier.
 88. Thecomposition of claim 87 having a cationic activity of greater than 20%.89. The composition of claim 88, wherein said cationic activity isgreater than 35%.
 90. The composition of claim 89, wherein said cationicactivity is greater than 50%.
 91. The composition as in any one ofclaims 49, 59, 64 and 80, which is a cosmetic or personal care productselected from the group consisting of shampoo, hair conditioner,sunscreen formulation, baby shampoo, baby bath product, hand dishwashingliquid, body wash, facial wash, non-woven toilette, baby wipe and bubblebath product.
 92. The composition of claim 91, wherein said cosmetic orpersonal care product is a non-aqueous topical formulation.
 93. Thecomposition of claim 91, wherein said cosmetic or personal care productis an aqueous topical formulation.